U.S. patent application number 13/016604 was filed with the patent office on 2011-08-18 for amide derivative, pest control agent containing the amide derivative, and use of the amide derivative.
This patent application is currently assigned to MITSUI CHEMICALS AGRO, INC.. Invention is credited to Yoji Aoki, Hidenori Daido, Yasuaki Fukazawa, Atsushi Hirabayashi, Mai Hirose, Hiroyuki Katsuta, Atsuko Kawahara, Yumi Kobayashi, Michikazu Nomura, Yusuke Takahashi, Hidetaka Tsukada.
Application Number | 20110201687 13/016604 |
Document ID | / |
Family ID | 44370086 |
Filed Date | 2011-08-18 |
United States Patent
Application |
20110201687 |
Kind Code |
A1 |
Kobayashi; Yumi ; et
al. |
August 18, 2011 |
AMIDE DERIVATIVE, PEST CONTROL AGENT CONTAINING THE AMIDE
DERIVATIVE, AND USE OF THE AMIDE DERIVATIVE
Abstract
An amide derivative represented by the following Formula (1) is
provided as an amide derivative showing a significantly excellent
effect for a pest control action. In the following Formula (1), A
represents a carbon atom, a nitrogen atom, or the like, and K
represents a non-metal atomic group necessary for forming a cyclic
linking group derived from benzene or a heterocyclie. X represents
a halogen atom or the like; n represents an integer of from 0 to 4.
R.sub.1 and R.sub.2 represent hydrogen atoms, alkyl groups, or the
like. T represents --C(=G.sub.1)-Q.sub.1 or
--C(=G.sub.1)-G.sub.2Q.sub.2, and G.sub.1 to G.sub.3 each represent
oxygen atoms or the like. Q.sub.1 and Q.sub.2 each represent a
hydrogen atom, an alkyl group, an aryl group, or the like. Y.sub.1
and Y.sub.5 each represent a halogen atom or the like, Y.sub.2 and
Y.sub.4 each represent a hydrogen atom or the like, and Y.sub.3
represents a C2-C5 haloalkyl group. ##STR00001##
Inventors: |
Kobayashi; Yumi;
(Mobara-shi, JP) ; Daido; Hidenori; (Otsu-shi,
JP) ; Katsuta; Hiroyuki; (Chiba-shi, JP) ;
Nomura; Michikazu; (Mobara-shi, JP) ; Tsukada;
Hidetaka; (Omuta-shi, JP) ; Hirabayashi; Atsushi;
(Omuta-shi, JP) ; Takahashi; Yusuke; (Omuta-shi,
JP) ; Aoki; Yoji; (Chiba-shi, JP) ; Kawahara;
Atsuko; (Mobara-shi, JP) ; Fukazawa; Yasuaki;
(Mobara-shi, JP) ; Hirose; Mai; (Chiba-shi,
JP) |
Assignee: |
MITSUI CHEMICALS AGRO, INC.
Tokyo
JP
|
Family ID: |
44370086 |
Appl. No.: |
13/016604 |
Filed: |
January 28, 2011 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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PCT/JP2009/061914 |
Jun 30, 2009 |
|
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13016604 |
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61329695 |
Apr 30, 2010 |
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Current U.S.
Class: |
514/616 ;
564/155 |
Current CPC
Class: |
A01N 37/22 20130101;
C07C 233/88 20130101; A61K 31/167 20130101; C07C 255/60 20130101;
C07C 255/57 20130101; A61P 33/14 20180101; C07D 213/82 20130101;
A01N 43/40 20130101; C07C 237/42 20130101; A01N 37/46 20130101;
A01N 43/78 20130101 |
Class at
Publication: |
514/616 ;
564/155 |
International
Class: |
A61K 31/167 20060101
A61K031/167; C07C 237/42 20060101 C07C237/42; A01N 37/22 20060101
A01N037/22; A61P 33/14 20060101 A61P033/14; A01P 7/02 20060101
A01P007/02 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 13, 2008 |
JP |
2008-208714 |
Jan 29, 2010 |
JP |
2010-019747 |
Claims
1. An amide derivative represented by the following Formula (1):
##STR00281## wherein, in Formula (1): A represents a carbon atom,
an oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a
sulfur atom; K represents a non-metal atom group necessary for
forming a cyclic linking group derived from benzene, pyridine,
pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine,
pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds; X represents a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9
halocycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6
alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group, a
C2-C6 haloalkenyloxy group, a C2-C6 alkynyloxy group, a C2-C6
haloalkynyloxy group, a C3-C9 cycloalkoxy group, a C3-C9
halocycloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylsulfonyloxy group, a C1-C6
haloalkylsulfonyloxy group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C3-C7 alkenylcarbonyl group, a C3-C7
haloalkenylcarbonyl group, a C3-C7 alkynylcarbonyl group, a C3-C7
haloalkynylcarbonyl group, a C4-C10 cycloalkylcarbonyl group, a
C4-C10 halocycloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy
group, a C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group, a
C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a
C3-C7 alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl
group, a C3-C7 alkynyloxycarbonyl group, a C3-C7
haloalkynyloxycarbonyl group, a C4-C10 cycloalkyloxycarbonyl group,
a C4-C10 halocycloalkyloxycarbonyl group, a C2-C7
alkylcarbonylamino group, a C2-C7 haloalkylcarbonylamino group, a
C2-C7 alkoxycarbonylamino group, a C2-C7 haloalkoxycarbonylamino
group, a C2-C7 alkoxycarbonyloxy group, a C2-C7
haloalkoxycarbonyloxy group, an arylcarbonylamino group, an amino
group, a carbamoyl group, a cyano group, a hydroxy group,
pentafluorosulfanyl group, a C1-C6 alkylamino group, a C1-C6
haloalkylamino group, a C2-C6 alkenylamino group, a C2-C6
haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloalkenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, a phenyl group, or a
heterocyclic group, and when there are plural X's, each X may be
the same as or different from an other; n represents an integer of
from 0 to 4; T represents --C(=G.sub.1)-Q.sub.1 or
--C(=G.sub.1)-G.sub.2Q.sub.2; G.sub.1 and G.sub.2 each
independently representing an oxygen atom or a sulfur atom; Q.sub.1
and Q.sub.2 each represent: a hydrogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C9
cycloalkyl group, a C3-C9 halocycloalkyl group, a benzyl group, a
phenyl group which may have a substituent, a naphthyl group, or a
heterocyclic group which may have a substituent; Y.sub.1 and
Y.sub.5 each independently represent a halogen atom, a C1-C6
haloalkoxy group, or a C1-C3 haloalkyl group; Y.sub.2 and Y.sub.4
each independently represent a hydrogen atom, a halogen atom, or a
C1-C4 alkyl group; Y.sub.3 represents a C2-C5 haloalkyl group;
wherein, in Q.sub.1 and Q.sub.2, the substituent of a phenyl group
which may have a substituent and a heterocyclic group which may
have a substituent represents one or more substituent selected from
a group consisting of: a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9 halocycloalkyl
group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6
alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a
C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6
haloalkenyloxy group, a C2-C6 alkynyloxy group, a C2-C6
haloalkynyloxy group, a C3-C9 cycloalkoxy group, a C3-C9
halocycloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C3-C7 alkenylcarbonyl group, a C3-C7
haloalkenylcarbonyl group, a C3-C7 alkynylcarbonyl group, a C3-C7
haloalkynylcarbonyl group, a C4-C10 cycloalkylcarbonyl group, a
C4-C10 halocycloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy
group, a C2-C7 haloalkylcarbonyloxy group, a C1-C6 alkylsulfonyloxy
group, a C1-C6 haloalkylsulfonyloxy group, a C2-C7 alkoxycarbonyl
group, a C2-C7 haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl
group, a C3-C7 haloalkenyloxycarbonyl group, a C3-C7
alkynyloxycarbonyl group, a C3-C7 haloalkynyloxycarbonyl group, a
C4-C10 cycloalkyloxycarbonyl group, a C4-C10
halocycloalkyloxycarbonyl group, a C2-C7 alkylcarbonylamino group,
a C2-C7 haloalkylcarbonylamino group, a C2-C7 alkoxycarbonylamino
group, a C2-C7 haloalkoxycarbonylamino group, a C1-C6 alkylamino
group, a C1-C6 haloalkylamino group, a C2-C6 alkenylamino group, a
C2-C6 haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloalkenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, an amino group, a carbamoyl
group, a cyano group, a nitro group, a hydroxy group,
pentafluorosulfanyl group, a phenyl group which may have a
substituent, and a heterocyclic group which may have a substituent,
and when there are two or more substituents, the substituents may
be the same as or different from each other; wherein, the
heterocyclic group in X, Q.sub.1, and Q.sub.2 represents a pyridyl
group, a pyridine-N-oxide group, a pyrimidinyl group, a pyrazinyl
group, a pyridazyl group, a furyl group, a thienyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a
pyrrolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl
group, or a tetrazolyl group; G.sub.3 represents an oxygen atom or
a sulfur atom; and R.sub.1 and R.sub.2 each independently
represents a hydrogen atom, an oxygen atom, a halogen atom, a
hydroxy group, a nitro group, a nitroso group, a trimethylsilyl
group, a t-butyldimethylsilyl group, a cyano group, an amino group,
a C1-C6 alkyl group which may have a substituent, a C1-C6 haloalkyl
group which may have a substituent, a C2-C7 alkylcarbonyl group, a
C2-C7 haloalkylcarbonyl group, a C2-C6 alkenyl group which may have
a substituent, a C2-C6 haloalkenyl group which may have a
substituent, a C2-C6 alkynyl group which may have a substituent, a
C2-C6 haloalkynyl group which may have a substituent, a C2-C7
alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C3-C7
alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl group, a
C3-C7 alkynyloxycarbonyl group, a C3-C7 haloalkynyloxycarbonyl
group, a phenoxycarbonyl group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C2-C7 alkylcarbonyloxy group,
a C2-C7 haloalkylcarbonyloxy group, a benzoyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7, wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, provided that the
amide derivative represented by Formula (1) is not one of (A) to
(I) below: (A) a case where, in Formula (1), K represents a
non-metal atom group necessary for forming a cyclic linking group
derived from pyridine in combination with A and two carbon atoms to
which A bonds, Y.sub.1 represents a halogen atom, Y.sub.5
represents a C1-C6 haloalkoxy group, and T is
--C(=G.sub.1)-Q.sub.1; (B) a case where in Formula (1), K
represents a non-metal atom group necessary for forming a cyclic
linking group derived from pyrrole, pyrazole, imidazole, oxazole,
isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole,
thiodiazole, or triazole, in combination with A and two carbon
atoms to which A bonds, Y.sub.1 and Y.sub.5 each independently
represent a halogen atom, and T is --C(=G.sub.1)-G.sub.2Q.sub.2;
(C) a case where in Formula (1), K represents a non-metal atom
group necessary for forming a cyclic linking group derived from
pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds, T represents --C(=G.sub.1)-Q.sub.1, Y.sub.1 is a halogen
atom, and Y.sub.5 represents a halogen atom or a haloalkoxy group;
(D) a case where the amide derivative is an amide compound
represented by the following Formula (2): ##STR00282## wherein in
Formula (2), Y.sub.2 to Y.sub.4, Q.sub.1, G.sub.1, G.sub.3,
R.sub.1, and R.sub.2 have the same definitions as Y.sub.2 to
Y.sub.4, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and R.sub.2,
respectively, in Formula (1), Y.sub.1 represents a halogen atom,
and Y.sub.5 represents a C1-C2 haloalkoxy group; (E) a case where
in Formula (2), Y.sub.1 and Y.sub.5 represent halogen atoms, all
X's represent hydrogen atoms, and Y.sub.3 represents a C2-C3
haloalkyl group; (F) a case where the amide derivative is an amide
derivative represented by the following Formula (3): ##STR00283##
wherein in Formula (3), Y.sub.1 and Y.sub.5 each independently
represent a halogen atom, X.sub.1 and X.sub.3 each independently
represent a hydrogen atom or a fluorine atom, Q.sub.1 has the same
definition as Q.sub.1 in Formula (1), R.sub.1 represents a hydrogen
atom or a methyl group, and Y.sub.3 represents a C3-C4
perfluoroalkyl group; (G) a case where the amide derivative is an
amide derivative represented by the following Formula (4):
##STR00284## wherein in Formula (4), X.sub.1 represents a fluorine
atom, X.sub.2, X.sub.3, and X.sub.4 represent hydrogen atoms,
Y.sub.1 and Y.sub.5 are different from each other and represent a
bromine atom or a trifluoromethoxy group, Y.sub.2 and Y.sub.4
represent hydrogen atoms, Y.sub.3 represents a heptafluoroisopropyl
group, Q.sub.1 represents a phenyl group or a 2-chloropyridin-3-yl
group, and R.sub.1 and R.sub.2 are different from each other, and
each represent a hydrogen atom or a methyl group, or alternatively,
X.sub.1 represents a fluorine atom, X.sub.2, X.sub.3, and X.sub.4
represent hydrogen atoms, Y.sub.1 and Y.sub.5 represent bromine
atoms, Y.sub.2 and Y.sub.4 represent hydrogen atoms, Y.sub.3
represents a pentafluoroethyl group, Q.sub.1 represents a
2-fluorophenyl group, and R.sub.1 and R.sub.2 each independently
represent a hydrogen atom or a methyl group; (H) a case where the
amide derivative is an amide derivative represented by the
following Formula (5): ##STR00285## wherein in Formula (5), Y.sub.1
and Y.sub.5 each independently represent a halogen atom, X.sub.1
represents a hydrogen atom or a fluorine atom, Q.sub.2 represents a
2,2,2-trichloroethyl group or a 3,3,3-trifluoro-n-propyl group, and
Y.sub.3 represents a C2-C4 haloalkyl group; and (I) a case where
the amide derivative is an amide derivative represented by the
following Formula (6): ##STR00286## wherein in Formula (6), Y.sub.1
and Y.sub.5 each independently represent a halogen atom, Q.sub.2
has the same definition as Q.sub.2 in Formula (1), R.sub.1
represents a hydrogen atom or a methyl group, and Y.sub.3
represents a C3-C4 haloalkyl group;
2. The amide derivative according to claim 1, which is represented
by the following Formula (7): ##STR00287## wherein in Formula (7),
n represents 4, and X, Y.sub.1 to Y.sub.5, Q.sub.1, G.sub.1,
G.sub.3, R.sub.1, and R.sub.2 have the same definitions as X,
Y.sub.1 to Y.sub.5, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and
R.sub.2, respectively, in Formula (1).
3. The amide derivative according to claim 2, which is represented
by the following Formula (8): ##STR00288## wherein in Formula (8),
Q.sub.1 represents a phenyl group which may have a substituent or a
pyridyl group which may have a substituent; X.sub.1, X.sub.2,
X.sub.3, and X.sub.4 each independently represent a hydrogen atom
or a fluorine atom; R.sub.1 and R.sub.2 each independently
represent a hydrogen atom or a C1-C3 alkyl group; Y.sub.1 and
Y.sub.5 each independently represent a halogen atom, a C1-C3
haloalkoxy group, or a C1-C3 haloalkyl group, Y.sub.2 and Y.sub.4
each independently represent a hydrogen atom, a halogen atom, or a
C1-C4 alkyl group, and Y.sub.3 represents a C3-C4 haloalkyl group;
in a case where Y.sub.1 and Y.sub.5 represent halogen atoms
simultaneously, at least one of X.sub.1 or X.sub.2 represents a
fluorine atom; and in a case where Y.sub.1 or Y.sub.5 represents a
C1-C3 haloalkoxy group, X.sub.2 represents a fluorine atom.
4. The amide derivative according to claim 3, wherein in Formula
(8), Y.sub.3 represents a C3-C4 perfluoroalkyl group.
5. The amide derivative according to claim 4, wherein in Formula
(8), Y.sub.1 and Y.sub.5 each independently represent a chlorine
atom, a bromine atom, an iodine atom, a trifluoromethoxy group, a
trifluoromethyl group, or a pentafluoroethyl group, and Y.sub.2 and
Y.sub.4 represent hydrogen atoms.
6. The amide derivative according to claim 5, wherein in Formula
(8), X.sub.1 and X.sub.2 each independently represent a hydrogen
atom or a fluorine atom, and X.sub.3 and X.sub.4 represent hydrogen
atoms.
7. The amide derivative according to claim 6, wherein in Formula
(8), R.sub.1 and R.sub.2 each independently represent a hydrogen
atom or a methyl group.
8. The amide derivative according to claim 7, wherein in Formula
(8), Q.sub.1 represents a phenyl group or a pyridyl group which may
have a substituent selected from a group consisting of a halogen
atom, a C1 haloalkyl group, a nitro group, and a cyano group.
9. The amide derivative according to claim 8, wherein in Formula
(8), the number of the substituents in Q.sub.1 is 1 or 2.
10. The amide derivative according to claim 2, wherein in Formula
(7), Y.sub.3 represents a C2-C4 perfluoroalkyl group, Y.sub.2 and
Y.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5 each
represent a halogen atom or a C1-C3 haloalkyl group, and either
Y.sub.1 or Y.sub.5 represents a C1-C3 haloalkyl group.
11. The amide derivative according to claim 10, wherein in Formula
(7), X.sub.1 to X.sub.4 each independently represent a hydrogen
atom, a halogen atom, or a cyano group.
12. The amide derivative according to claim 1, which is represented
by the following Formula (9): ##STR00289## wherein in Formula (9),
n is 4, X, Y.sub.1 to Y.sub.5, Q.sub.2, G.sub.1 to G.sub.3,
R.sub.1, and R.sub.2 have the same definitions as X, Y.sub.1 to
Y.sub.5, Q.sub.2, G.sub.1 to G.sub.3, R.sub.1, and R.sub.2,
respectively, in Formula (1).
13. The amide derivative according to claim 12, wherein in Formula
(9), Y.sub.3 represents a C2-C4 perfluoroalkyl group, Y.sub.2 and
Y.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5 each
represent a halogen atom or a C1-C3 haloalkyl group, and either
Y.sub.1 or Y.sub.5 represents a C1-C3 haloalkyl group.
14. The amide derivative according to claim 13, wherein in Formula
(9), X.sub.1 to X.sub.4 each independently represent a hydrogen
atom, a halogen atom, or a cyano group.
15. The amide derivative according to claim 1, wherein in Formula
(1), K represents a non-metal atom group necessary for forming a
cyclic linking group derived from pyridine, pyridine-N-oxide,
pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole,
imidazole, oxazole, isoxazole, thiazole, isothiazole, furan,
thiophene, oxadiazole, thiodiazole, or triazole, in combination
with A and two carbon atoms to which A bonds.
16. The amide derivative according to claim 15, wherein in Formula
(1), Y.sub.3 represents a C2-C4 perfluoroalkyl group, Y.sub.2 and
Y.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5 each
represent a halogen atom or a C1-C3 haloalkyl group, and either
Y.sub.1 or Y.sub.5 represents a C 1-C3 haloalkyl group.
17. The amide derivative according to claim 16, wherein in Formula
(1), K represents a non-metal atom group necessary for forming a
cyclic linking group derived from pyridine, pyridine-N-oxide,
pyrrole, thiazole, furan, or thiophene, in combination with A and
two carbon atoms to which A bonds.
18. A pest control agent comprising at least one amide derivative
according to claim 1 as an active ingredient.
19. A pest controlling method comprising applying the pest control
agent according to claim 18 to a pest.
20. A composition for controlling a pest comprising as an active
ingredient at least one amide derivative represented by the
following Formula (A1): ##STR00290## wherein, in Formula (A1),
Q.sub.1 represents a phenyl group or a phenyl group substituted
with a halogen atom; X.sub.1 represents a fluorine atom; X.sub.2,
X.sub.3, and X.sub.4 are each a hydrogen atom; R.sub.1 represents a
hydrogen atom or a C1-C3 alkyl group; R.sub.2 is a hydrogen atom;
Y.sub.1 and Y.sub.5 each independently represent a halogen atom or
a C1-C3 haloalkyl group; Y.sub.2 and Y.sub.4 each represent a
hydrogen atom; and Y.sub.3 represents a heptafluoroisopropyl
group.
21. The composition according to claim 20, wherein the pest is an
animal parasite.
22. The composition according to claim 21, wherein in Formula (A1),
Q.sub.1 represents a phenyl group or a phenyl group substituted
with a single fluorine atom; R.sub.1 represents a hydrogen atom or
a methyl group; and Y.sub.1 and Y.sub.5 each independently
represent a bromine or iodine atom or a trifluoromethyl group.
23. The composition according to claim 22, wherein the amide
derivative represented by Formula (A1) is
2-fluoro-3-(N-methylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluor-
opropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluorobenzamide)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoro-
propan-2-yl)phenyl)benzamide, or
2-fluoro-3-(N-methylbenzamide)-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)p-
henyl)benzamide.
24. A method for exterminating animal parasites, comprising
administering to an animal the composition according to claim
21.
25. The method according to claim 24, wherein the animal parasite
is an ectoparasite.
26. The method according to claim 25, wherein the ectoparasite is
Siphonaptera pests.
27. The method according to claim 25, wherein the ectoparasite is
Acarina pests.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation-in-part application of
PCT Application PCT/JP2009/061914, filed Jun. 30, 2009, and claims
the benefit of U.S. provisional Application No. 61/329,695, filed
Apr. 30, 2010, the disclosures of which are incorporated by
reference herein. This application also claims priority under 35
USC 119 from Japanese patent Application No. 2008-208714, filed on
Aug. 13, 2008 and Japanese patent Application No. 2010-019747,
filed on Jan. 29, 2010, the disclosures of which are incorporated
by reference herein.
BACKGROUND OF THE INVENTION
[0002] 1. Field of the Invention
[0003] The present invention relates to a pest control agent, an
amide derivative contained in the pest control agent, and a method
for using the amide derivative.
[0004] 2. Description of the Related Art
[0005] Various amide derivatives are described in the pamphlets of
International Publication WO 2005/21488, International Publication
WO 2005/73165, International Publication WO 2006/137376, and
International Publication WO 2006/137395.
SUMMARY OF THE INVENTION
[0006] In the production of, for example, agricultural and
horticultural crops, due to causes such as currently-occurring
large scale damage due to pests or the like and the propagation of
pests having resistance to existing chemicals, there is a demand
for a novel agricultural/horticultural pest control agent.
[0007] It is an object of the present invention to provide an amide
derivative showing a pesticidal effect against a wide range of
agricultural/horticultural pests, a pest control agent containing
the amide derivative as an active ingredient, and a pest
controlling method.
[0008] The present inventors have conducted intensive studies to
develop a novel pest control agent, and as a result, they have
found that the aromatic carboxamide derivative represented by
Formula (1) of the present invention is a novel compound unknown in
the literature, and it is also a pest control agent, particularly
an agricultural/horticultural pest control agent, showing a
particularly high efficiency, thereby completing the present
invention.
[0009] Further, they have also discovered a novel preparation
method and a useful intermediate for the preparation of the
compound of the present invention. As a result, they have completed
the present invention.
[0010] That is, the present invention is as follows.
[0011] <1> An amide derivative represented by the following
Formula (1):
[0012] 1. An amide derivative represented by the following Formula
(1):
##STR00002##
[0013] Wherein, in Formula (1), A represents a carbon atom, an
oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a
sulfur atom. K represents a non-metal atom group necessary for
forming a cyclic linking group derived from benzene, pyridine,
pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine,
pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds.
[0014] X represents a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9
halocycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6
alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group, a
C2-C6 haloalkenyloxy group, a C2-C6 alkynyloxy group, a C2-C6
haloalkynyloxy group, a C3-C9 cycloalkoxy group, a C3-C9
halocycloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylsulfonyloxy group, a C1-C6
haloalkylsulfonyloxy group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C3-C7 alkenylcarbonyl group, a C3-C7
haloalkenylcarbonyl group, a C3-C7 alkynylcarbonyl group, a C3-C7
haloalkynylcarbonyl group, a C4-C10 cycloalkylcarbonyl group, a
C4-C10 halocycloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy
group, a C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group, a
C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a
C3-C7 alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl
group, a C3-C7 alkynyloxycarbonyl group, a C3-C7
haloalkynyloxycarbonyl group, a C4-C10 cycloalkyloxycarbonyl group,
a C4-C10 halocycloalkyloxycarbonyl group, a C2-C7
alkylcarbonylamino group, a C2-C7 haloalkylcarbonylamino group, a
C2-C7 alkoxycarbonylamino group, a C2-C7 haloalkoxycarbonylamino
group, a C2-C7 alkoxycarbonyloxy group, a C2-C7
haloalkoxycarbonyloxy group, an arylcarbonylamino group, an amino
group, a carbamoyl group, a cyano group, a hydroxy group,
pentafluorosulfanyl group, a C1-C6 alkylamino group, a C1-C6
haloalkylamino group, a C2-C6 alkenylamino group, a C2-C6
haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloalkenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, a phenyl group, or a
heterocyclic group, and when there are plural X's, each X may be
the same as or different from an other.
[0015] n represents an integer of from 0 to 4.
[0016] T represents --C(=G.sub.1)-Q.sub.1 or
--C(=G1)-G.sub.2Q.sub.2.
[0017] G.sub.1 and G.sub.2 each independently represent an oxygen
atom or a sulfur atom,
[0018] Q.sub.1 and Q.sub.2 each represent a hydrogen atom, a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a
C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl
group, a C3-C9 cycloalkyl group, a C3-C9 halocycloalkyl group, a
benzyl group, a phenyl group which may have a substituent, a
naphthyl group, or a heterocyclic group which may have a
substituent.
[0019] Y.sub.1 and Y.sub.5 each independently represent a halogen
atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group, Y.sub.2
and Y.sub.4 each independently represent a hydrogen atom, a halogen
atom, or a C1-C4 alkyl group, Y.sub.3 represents a C2-C5 haloalkyl
group.
[0020] Wherein in Q.sub.1 and Q.sub.2, the substituent of a phenyl
group which may have a substituent and a heterocyclic group which
may have a substituent represents one or more substituent selected
from a group consisting of a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9
halocycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6
alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group, a
C2-C6 haloalkenyloxy group, a C2-C6 alkynyloxy group, a C2-C6
haloalkynyloxy group, a C3-C9 cycloalkoxy group, a C3-C9
halocycloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C3-C7 alkenylcarbonyl group, a C3-C7
haloalkenylcarbonyl group, a C3-C7 alkynylcarbonyl group, a C3-C7
haloalkynylcarbonyl group, a C4-C10 cycloalkylcarbonyl group, a
C4-C10 halocycloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy
group, a C2-C7 haloalkylcarbonyloxy group, a C1-C6 alkylsulfonyloxy
group, a C1-C6 haloalkylsulfonyloxy group, a C2-C7 alkoxycarbonyl
group, a C2-C7 haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl
group, a C3-C7 haloalkenyloxycarbonyl group, a C3-C7
alkynyloxycarbonyl group, a C3-C7 haloalkynyloxycarbonyl group, a
C4-C10 cycloalkyloxycarbonyl group, a C4-C10
halocycloalkyloxycarbonyl group, a C2-C7 alkylcarbonylamino group,
a C2-C7 haloalkylcarbonylamino group, a C2-C7 alkoxycarbonylamino
group, a C2-C7 haloalkoxycarbonylamino group, a C1-C6 alkylamino
group, a C1-C6 haloalkylamino group, a C2-C6 alkenylamino group, a
C2-C6 haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloallcenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, an amino group, a carbamoyl
group, a cyano group, a nitro group, a hydroxy group,
pentafluorosulfanyl group, a phenyl group which may have a
substituent, and a heterocyclic group which may have a substituent,
and when there are two or more substituents, the substituents may
be the same as or different from each other.
[0021] Wherein the heterocyclic group in X, Q.sub.1, and Q.sub.2
represent a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyrazinyl group, a pyridazyl group, a furyl group, a
thienyl group, an oxazolyl group, an isoxazolyl group, an
oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a
thiadiazolyl group, a pyrrolyl group, an imidazolyl group, a
triazolyl group, a pyrazolyl group, or a tetrazolyl group.
[0022] G.sub.3 represents an oxygen atom or a sulfur atom.
[0023] R.sub.1 and R.sub.2 each independently represent a hydrogen
atom, an oxygen atom, a halogen atom, a hydroxy group, a nitro
group, a nitroso group, a trimethylsilyl group, a
t-butyldimethylsilyl group, a cyano group, an amino group, a C1-C6
alkyl group which may have a substituent, a C1-C6 haloalkyl group
which may have a substituent, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C2-C6 alkenyl group which may have a
substituent, a C2-C6 haloalkenyl group which may have a
substituent, a C2-C6 alkynyl group which may have a substituent, a
C2-C6 haloalkynyl group which may have a substituent, a C2-C7
alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C3-C7
alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl group, a
C3-C7 alkynyloxycarbonyl group, a C3-C7 haloalkynyloxycarbonyl
group, a phenoxycarbonyl group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C2-C7 alkylcarbonyloxy group,
a C2-C7 haloalkylcarbonyloxy group, a benzoyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7, wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group.
[0024] However the amide derivative represented by Formula (1) is
not one of (A) to (I).
[0025] (A) A case where, in Formula (1), K represents a non-metal
atom group necessary for forming a cyclic linking group derived
from pyridine in combination with A and two carbon atoms to which A
bonds, Y.sub.1 represents a halogen atom, and Y.sub.5 represents a
C1-C6 haloalkoxy group, and T is --C(=G.sub.1)-Q.sub.1.
[0026] (B) A case where, in Formula (1), K represents a non-metal
atom group necessary for forming a cyclic linking group derived
from pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds, Y.sub.1 and Y.sub.5 represent each independently a halogen
atom, and T is --C(=G.sub.1)-G.sub.2Q.sub.2.
[0027] (C) A case where, in Formula (1), K represents a non-metal
atom group necessary for forming a cyclic linking group derived
from pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds, T represents --C(=G.sub.1)-Q.sub.1, Y.sub.1 is a halogen
atom, and Y.sub.5 represents a halogen atom or a haloalkoxy
group.
[0028] (D) A case where, the amide derivative is an amide compound
represented by the following Formula (2):
##STR00003##
[0029] Wherein in Formula (2), Y.sub.2 to Y.sub.4, Q.sub.1,
G.sub.1, G.sub.3, R.sub.1, and R.sub.2 have the same definitions as
Y.sub.2 to Y.sub.4, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and
R.sub.2, respectively, in Formula (1), Y.sub.1 represents a halogen
atom, and Y.sub.5 represents a C1-C2 haloalkoxy group.
[0030] (E) A case where, in Formula (2), Y.sub.1 and Y.sub.5 each
independently represent a halogen atom, all X's represent hydrogen
atoms, and Y.sub.3 represents a C2-C3 haloalkyl group.
[0031] (F) A case where, the amide derivative is an amide
derivative represented by the following Formula (3)
##STR00004##
[0032] Wherein in Formula (3), Y.sub.1 and Y.sub.5 each
independently represent a halogen atom, X.sub.1 and X.sub.3 each
independently represent a hydrogen atom or a fluorine atom, Q.sub.1
has the same definition as Q.sub.1 in Formula (1), R.sub.1
represents a hydrogen atom or a methyl group, and Y.sub.3
represents a C3-C4 perfluoroalkyl group.
[0033] (G) A case where the amide derivative is an amide derivative
represented by the following Formula (4):
##STR00005##
[0034] Wherein in Formula (4), X.sub.1 represents a fluorine atom,
X.sub.2, X.sub.3, and X.sub.4 represent hydrogen atoms, Y.sub.1 and
Y.sub.5 are different from each other and represent a bromine atom
or a trifluoromethoxy group, Y.sub.2 and Y.sub.4 represent hydrogen
atoms, Y.sub.3 represents a heptafluoroisopropyl group, Q.sub.1
represents a phenyl group or a 2-chloropyridin-3-yl group, and
R.sub.1 and R.sub.2 are different from each other, and each
represent a hydrogen atom or a methyl group.
[0035] Alternatively, X.sub.1 represents a fluorine atom, X.sub.2,
X.sub.3, and X.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5
represent bromine atoms, Y.sub.2 and Y.sub.4 represent hydrogen
atoms, Y.sub.3 represents a pentafluoroethyl group, Q.sub.1
represents a 2-fluorophenyl group, and R.sub.1 and R.sub.2 each
independently represent a hydrogen atom or a methyl group}.
[0036] (H) A case where, the amide derivative is an amide
derivative represented by the following Formula (5):
##STR00006##
[0037] Wherein, in Formula (5), Y.sub.1 and Y.sub.5 each
independently represent a halogen atom, X.sub.1 represents a
hydrogen atom or a fluorine atom, Q.sub.2 represents a
2,2,2-trichloroethyl group or a 3,3,3-trifluoro-n-propyl group, and
Y.sub.3 represents a C2-C4 haloalkyl group.
[0038] (I) A case where the amide derivative is an amide derivative
represented by the following Formula (6):
##STR00007##
[0039] Wherein, in Formula (6), Y.sub.1 and Y.sub.5 each
independently represent a halogen atom, Q.sub.2 has the same
definition as Q.sub.2 in Formula (1), R.sub.1 represents a hydrogen
atom or a methyl group, and Y.sub.3 represents a C3-C4 haloalkyl
group.
[0040] <2> The amide compound according to <1>, which
is represented by the following Formula (7):
##STR00008##
[0041] Wherein, in Formula (7), n represents 4, and X, Y.sub.1 to
Y.sub.5, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and R.sub.2 have the
same definitions as X, Y.sub.1 to Y.sub.5, Q.sub.1, G.sub.1,
G.sub.3, R.sub.1, and R.sub.2, respectively, in Formula (1).
[0042] <3> The amide derivative according to <2>, which
is represented by the following Formula (8):
##STR00009##
[0043] Wherein, in Formula (8), Q.sub.1 represents a phenyl group
which may have a substituent or a pyridyl group which may have a
substituent.
[0044] X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently
represent a hydrogen atom or a fluorine atom.
[0045] R.sub.1 and R.sub.2 each independently represent a hydrogen
atom or a C1-C3 alkyl group.
[0046] Y.sub.1 and Y.sub.5 each independently represent a halogen
atom, a C1-C3 haloalkoxy group, or a C1-C3 haloalkyl group, Y.sub.2
and Y.sub.4 each independently represent a hydrogen atom, a halogen
atom, or a C1-C4 alkyl group, and Y.sub.3 represents a C3-C4
haloalkyl group.
[0047] In a case where Y.sub.1 and Y.sub.5 represent halogen atoms
simultaneously, at least one of X.sub.1 and X.sub.2 represents a
fluorine atom. Further, in a case where Y.sub.1 or Y.sub.5
represents a C1-C3 haloalkoxy group, X.sub.2 represents a fluorine
atom.
[0048] <4> The amide derivative according to <3>,
wherein in Formula (8), Y.sub.3 represents a C3-C4 perfluoroalkyl
group.
[0049] <5> The amide derivative according to <4>,
wherein in Formula (8), Y.sub.1 and Y.sub.5 each independently
represent a chlorine atom, a bromine atom, an iodine atom, a
trifluoromethoxy group, a trifluoromethyl group, or a
pentafluoroethyl group, and Y.sub.2 and Y.sub.4 represent hydrogen
atoms.
[0050] <6> The amide derivative according to <5>,
wherein in Formula (8), X.sub.1 and X.sub.2 each independently
represent a hydrogen atom or a fluorine atom, and X.sub.3 and
X.sub.4 represent hydrogen atoms.
[0051] <7> The amide derivative according to <6>,
wherein in Formula (8), R.sub.1 and R.sub.2 each independently
represent a hydrogen atom or a methyl group.
[0052] <8> The amide derivative according to claim 7, wherein
in Formula (8), Q.sub.1 represents a phenyl group or a pyridyl
group which may have a substituent selected from a group consisting
of a halogen atom, a C1 haloalkyl group, a nitro group, and a cyano
group.
[0053] <9> The amide derivative according to claim 8, wherein
in Formula (8), the number of the substituents in Q.sub.1 is 1 or
2.
[0054] <10> The amide derivative according to <9>,
wherein in Formula (8), Q.sub.1 represents a phenyl group, a
2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl
group, a 2-chlorophenyl group, a 3-chlorophenyl group, a
4-chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group,
a 4-bromophenyl group, a 2-iodophenyl group, a 3-iodophenyl group,
a 4-iodophenyl group, a (2-triofluoromethyl)phenyl group, a
(3-triofluoromethyl)phenyl group, a (4-triofluoromethyl)phenyl
group, a 2-nitrophenyl group, a 3-nitrophenyl group, a
4-nitrophenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group,
a 4-cyanophenyl group, a 2,6-difluorophenyl group, a
3,4-dichlorophenyl group, a 2,4-dichlorophenyl group, a
2-chloro-4-fluorophenyl group, a 2-chloro-4,5-difluorophenyl group,
a 4-bromo-2-chlorophenyl group, a 2-bromo-4-chlorophenyl group, a
2-bromo-4-fluorophenyl group, a 2-chloro-4-nitorophenyl group, a
3,5-dicyanophenyl group, a 4-cyano-2-fluorophenyl group, a
2-chloro-4-cyanophenyl group, a pyridin-3-yl group, a
2-fluoropyridin-3-yl group, a 2-chloropyridin-3-yl group, a
2-bromopyridin-3-yl group, a 2-iodopyridin-3-yl group, a
2-(trifluoromethyl)pyridin-3-yl group, a 2-nitoropyridin-3-yl
group, a 2-cyanopyridin-3-yl group, a 6-fluoropyridin-3-yl group, a
6-chloropyridin-3-yl group, a 6-bromopyridin-3-yl group, a
6-iodopyridin-3-yl group, a 6-(trifluoromethyl)pyridin-3-yl group,
a 6-nitoropyridin-3-yl group, a 6-cyanopyridin-3-yl group, a
5-fluoropyridin-3-yl group, a 5-chloropyridin-3-yl group, a
5-bromopyridin-3-yl group, a 5-iodopyridin-3-yl group, a
5-(trifluoromethyl)pyridin-3-yl group, a 5-nitoropyridin-3-yl
group, a 5-cyanopyridin-3-yl group, a 4-fluoropyridin-3-yl group, a
4-chloropyridin-3-yl group, a 4-bromopyridin-3-yl group, a
4-iodopyridin-3-yl group, a 4-(trifluoromethyl)pyridin-3-yl group,
a 4-nitoropyridin-3-yl group, a 4-cyanopyridin-3-yl group, a
2,6-dichloropyridin-3-yl group, a pyridin-3-yl N-oxide group, a
pyridin-4-yl group, a 2-chloropyridin-4-yl group, a
3-bromopyridin-4-yl group, a 3,5-dichloropyridin-4-yl group, a
3-(trifluoromethyl)pyridine-4-yl group, a 2,6-dicyanopyridin-4-yl
group, a pyridin-4-yl N-oxide group, a pyridin-2-yl group, a
3-chloropyridin-2-yl group, a 4-bromopyridin-2-yl group, a
5-iodopyridin-2-yl group, a 6-chloropyridin-2-yl group, or a
4-cyanopyridin-2-yl group,
[0055] <11> The amide derivative according to <10>,
wherein the compound represented by Formula (8) is
3-benzamido-N-(2-bromo-6-chloro-4-(perfluoropropan-2-yl)phenyl)-2-fluorob-
enzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamo-
yl)-2-fluorophenyl)nicotinamide,
3-(4-cyano-N-methylbenzamido)-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phen-
yl)-2-fluorobenzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-flu-
orophenyl)-N-methylnicotinamide,
3-benzamido-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzami-
de,
3-benzamido-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoroben-
zamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methy-
lbenzamido)benzamide,
6-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-flu-
orophenyl)-N-methylnicotinamide,
3-(3-cyano-N-methylbenzamido)-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phen-
yl)-2-fluorobenzamide,
N-(2,6-dichloro-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenza-
mido)benzamide,
3-(4-cyano-N-methylbenzamido)-N-(2,6-dichloro-4-(perfluoropropan-2-yl)phe-
nyl)-2-fluorobenzamide,
2-chloro-N-(3-(2,6-dichloro-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fl-
uorophenyl)-N-methylnicotinamide,
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenzami-
do)benzamide,
3-(4-cyano-N-methylbenzamido)-N-(2,6-diiodo-4-(perfluoropropan-2-yl)pheny-
l)-2-fluorobenzamide,
3-benzamido-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluorobenzami-
de,
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenz-
amido)benzamide,
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenzami-
do)benzamide,
3-(2,6-difluorobenzamido)-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-
-fluorobenzamide,
N-(2-bromo-6-iodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylben-
zamido)benzamide,
N-(3-(2-bromo-6-iodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluorophe-
nyl)-2-chloro-N-methylnicotinamide,
[0056]
3-(4-cyanobenzamido)-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)--
2-fluorobenzamide,
3-(3-cyanobenzamido)-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluo-
robenzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(N-methylbenzami-
do)benzamide,
3-(4-cyano-N-methylbenzamido)-N-(2,6-dibromo-4-(perfluorobutan-2-yl)pheny-
l)-2-fluorobenzamide,
3-(3-cyano-N-methylbenzamido)-N-(2,6-dibromo-4-(perfluorobutan-2-yl)pheny-
l)-2-fluorobenzamide,
6-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)-N-methylnicotinamide,
3-benzamido-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluorobenzamid-
e,
3-(3-cyanobenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-flu-
orobenzamide,
3-(4-cyanobenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluor-
obenzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(N-methylbenzamid-
o)benzamide,
3-(3-cyano-N-methylbenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl-
)-2-fluorobenzamide,
3-(4-cyano-N-methylbenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl-
)-2-fluorobenzamide,
3-benzamido-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)benzamide,
2-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)n-
icotinamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)n-
icotinamide,
3-cyano-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)be-
nzamide,
3-(4-cyanobenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-
benzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-
-2-fluorobenzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-3-(3-fluorobenzamido)benzami-
de,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-3-(4-fluorobenzamido)benz-
amide,
[0057]
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2,6-
-difluorobenzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-N-methylb-
enzamide,
2-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl-
)phenyl)-N-methylnicotinamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)--
N-methylnicotinamide,
3-cyano-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-N-
-methylbenzamide,
4-cyano-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-N-
-methylbenzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2-fluoro--
N-methylbenzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-3-fluoro--
N-methylbenzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-4-fluoro--
N-methylbenzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2,6-diflu-
oro-N-methylbenzamide,
2-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluor-
ophenyl)nicotinamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluor-
ophenyl)nicotinamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenzamid-
o)benzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(3-fluorobenzamid-
o)benzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenzamid-
o)benzamide,
difluorobenzamido)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluorob-
enzamide,
3-benzamido-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)benzami-
de,
6-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phen-
yl)nicotinamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2-fluoro-
benzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamo-
yl)phenyl)nicotinamide,
[0058]
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-(3-fluorobenzamido)-
benzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-(4-fluorobenzam-
ido)benzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2,6-difl-
uorobenzamide,
3-cyano-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)b-
enzamide,
3-(4-cyanobenzamido)-N-(2,6-dibromo-4-(perfluorobutan-2-yl)pheny-
l)benzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)-N-methylnicotinamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluor-
ophenyl)-N-methylnicotinamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluorophenyl)--
2-fluoro-N-methylbenzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-methy-
lbenzamido)benzamide,
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(4-fluoro-N-methy-
lbenzamido)benzamide,
N-(3-(2,6-diiodo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluorophenyl)--
2,6-difluoro-N-methylbenzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-N-methyl-
benzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamo-
yl)phenyl)-N-methylnicotinamide,
6-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-
-N-methylnicotinamide,
3-cyano-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)--
N-methylbenzamide,
4-cyano-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)--
N-methylbenzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2-fluoro-
-N-methylbenzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-3-fluoro-
-N-methylbenzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-4-fluoro-
-N-methylbenzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)phenyl)-2,6-difl-
uoro-N-methylbenzamide,
[0059]
2-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)--
2-fluorophenyl)nicotinamide,
6-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)nicotinamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenzami-
do)benzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(3-fluorobenzami-
do)benzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenzami-
do)benzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-(2,6-difluorobenzamido)-2-
-fluorobenzamide,
2-chloro-N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)nicotinamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)nicotinamide,
3-(3-cyanobenzamido)-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluo-
robenzamide,
3-(4-cyanobenzamido)-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluo-
robenzamide,
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluorobenzami-
do)benzamide,
2-chloro-N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)-N-methylnicotinamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluorophenyl)-
-2-fluoro-N-methylbenzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-meth-
ylbenzamido)benzamide,
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(4-fluoro-N-meth-
ylbenzamido)benzamide,
N-(3-(2,6-dibromo-4-(perfluorobutan-2-yl)phenylcarbamoyl)-2-fluorophenyl)-
-2,6-difluoro-N-methylbenzamide,
3-(3-cyano-N-methylbenzamido)-N-(2,6-diiodo-4-(perfluoropropan-2-yl)pheny-
l)-2-fluorobenzamide,
N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluorophenyl)-
-2-fluoro-N-methylbenzamide,
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-meth-
ylbenzamido)benzamide,
6-chloro-N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)-N-methylnicotinamide,
[0060]
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluoro--
N-methylbenzamido)benzamide,
N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluorophenyl)-
-2,6-difluoro-N-methylbenzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenzam-
ido)benzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluorobenzam-
ido)benzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenzam-
ido)benzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-3-(2,6-difluorobenzamido)--
2-fluorobenzamide,
6-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-flu-
orophenyl)nicotinamide,
3-(3-cyanobenzamido)-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-flu-
orobenzamide,
3-(4-cyanobenzamido)-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-flu-
orobenzamide,
2-chloro-N-(3-(2,6-diiodo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluo-
rophenyl)-N-methylnicotinamide,
N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluorophenyl-
)-2-fluoro-N-methylbenzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-met-
hylbenzamido)benzamide,
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluoro-N-met-
hylbenzamido)benzamide,
N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-fluorophenyl-
)-2,6-difluoro-N-methylbenzamide,
3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)pheny-
l)-2-fluorobenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenylcarbamoy-
l)-2-fluorophenyl)-2-chloronicotinamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-3-(4-cyan-
obenzamido)-2-fluorobenzamide,
3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-chloronicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-chloro-N-methylnicotinamide,
3-benzamido-N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)pheny-
l)benzamide,
2-chloro-N-(3-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)pheny-
lcarbamoyl)phenyl)nicotinamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano-
benzamido)benzamide,
[0061]
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-
-cyanobenzamido)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-3-cyano-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-4-cyano-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-fluoro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-N-methyl-4-nitrobenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-6-chloro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-6-cyano-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-N-methyl-3-nitrobenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N-methyl-3-
-(N-methylbenzamido)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)(methyl)-
carbamoyl)phenyl)-2-chloro-N-methylnicotinamide,
2-bromo-N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)nicotinamide,
2-chloro-N-(3-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)pheny-
lcarbamoyl)phenyl)-N-methylnicotinamide,
N-(3-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoy-
l)phenyl)-4-cyano-N-methylbenzamide,
3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-4-fluorobenzamide,
N-(5-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-chloronicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)(methyl)-
carbamoyl)phenyl)-2-chloronicotinamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-
-(N-methylbenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
-N-methylbenzamido)-4-fluorobenzamide,
N-(5-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-chloro-N-methylnicotinamide,
3-benzamido-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phenyl)be-
nzamide,
[0062]
2-chloro-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phe-
nylcarbamoyl)phenyl)nicotinamide,
N-methyl-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phenylcar-
bamoyl)phenyl)benzamide,
2-chloro-N-methyl-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenylcarbamoyl)phenyl)nicotinamide,
3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano-
benzamido)-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
benzamido)-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano-
-N-methylbenzamido)-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
-N-methylbenzamido)-N-methylbenzamide,
2-bromo-N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylnicotinamide,
3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-2-fluorobenzamide,
2-bromo-N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)(methyl)carbamoyl)phenyl)nicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-chloronicotinamide,
3-benzamido-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-
benzamide,
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluorometh-
yl)phenylcarbamoyl)phenyl)nicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-4-cyano-2-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-4-cyano-2-fluorobenzamide,
3-cyano-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phenylcarb-
amoyl)phenyl)benzamide,
3-(4-cyanobenzamido)-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenyl)benzamide,
3-cyano-N-methyl-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)p-
henylcarbamoyl)phenyl)benzamide,
4-cyano-N-methyl-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)p-
henylcarbamoyl)phenyl)benzamide,
[0063]
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-
-cyanobenzamido)-2-fluorobenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-chloro-N-methylnicotinamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
-N-methylbenzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(N-methylbenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano-
-N-methylbenzamido)-2-fluorobenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-chloro-4-cyano-N-methylbenzamide,
3-benzamido-N-methyl-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenyl)benzamide,
2-chloro-N-(3-(methyl(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)ph-
enyl)carbamoyl)phenyl)nicotinamide,
3-(3-cyanobenzamido)-N-methyl-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluo-
romethyl)phenyl)benzamide,
2-bromo-N-(3-(methyl(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phe-
nyl)carbamoyl)phenyl)nicotinamide,
2-bromo-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)phenylcarb-
amoyl)phenyl)nicotinamide,
2-bromo-N-methyl-N-(3-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)p-
henylcarbamoyl)phenyl)nicotinamide,
3-(4-cyanobenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenyl)benzamide,
3-cyano-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)benzamide,
2-bromo-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)nicotinamide,
4-cyano-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)-N-methylbenzamide,
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-iodonicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-6-fluoro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-4-cyano-2-fluoro-N-methylbenzamide,
[0064]
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcar-
bamoyl)-2-fluorophenyl)-6-chloro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-3,5-dicyano-N-methylbenzamide,
3-benzamido-2-fluoro-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenyl)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-3,5-dicyano-N-methylbenzamide,
3-benzamido-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenyl)benzamide,
2-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)nicotinamide,
3-benzamido-N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-
-2-fluorobenzamide,
3-benzamido-N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-
-2-fluorobenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
-2-fluorophenyl)-2-chloronicotinamide,
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-3-(4-cyanob-
enzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3--
(N-methylbenzamido)benzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano--
N-methylbenzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano--
N-methylbenzamido)-2-fluorobenzamide,
2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
(N-methylbenzamido)benzamide,
3-(4-cyano-N-methylbenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-
-6-(trifluoromethyl)phenyl)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-N-methylbenzamide,
3-benzamido-N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-
benzamide,
3-benzamido-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(-
N-methylbenzamido)benzamide,
3-(4-cyano-N-methylbenzamido)-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)--
6-(trifluoromethyl)phenyl)benzamide,
[0065]
3-(3-cyano-N-methylbenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-
-2-yl)-6-(trifluoromethyl)phenyl)benzamide,
2-fluoro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)-N-methylbenzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)benzamide,
2,6-difluoro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluorom-
ethyl)phenylcarbamoyl)phenyl)-N-methylbenzamide,
6-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)nicotinamide,
3-(3-cyanobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
3-(4-cyanobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
2-fluoro-3-(2-fluorobenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trif-
luoromethyl)phenyl)benzamide,
2-fluoro-3-(3-fluorobenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trif-
luoromethyl)phenyl)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2,6-difluoro-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(3-fluoro-N-methylbenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(4-fluoro-N-methylbenzamido)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-2-chloronicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-6-chloronicotinamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyano-
benzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(2-fluorobenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(3-fluorobenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(4-fluorobenzamido)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-N-methylnicotinamide,
2-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)-N-methylnicotinamide,
[0066]
2-fluoro-3-(4-fluorobenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl)-6-
-(trifluoromethyl)phenyl)benzamide,
3-(2,6-difluorobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(-
trifluoromethyl)phenyl)benzamide,
6-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-6-chloronicotinamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-fluorobenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-fluor-
obenzamido)benzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-fluor-
obenzamido)benzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2,6-difluorobenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(2,6-dif-
luorobenzamido)-2-fluorobenzamide,
3-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)benzamide,
3-(4-fluorobenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluorometh-
yl)phenyl)benzamide,
2-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)benzamide,
2,6-difluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phe-
nylcarbamoyl)phenyl)benzamide,
6-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)nicotinamide,
6-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylnicotinamide,
3-cyano-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)-N-methylbenzamide,
2-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylbenzamide,
3-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylbenzamide,
4-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-fluoro-N-methylbenzamide,
[0067]
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcar-
bamoyl)phenyl)-3-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-4-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2,6-difluoro-N-methylbenzamide,
2,4-dichloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phe-
nylcarbamoyl)phenyl)benzamide,
3-(2,4-dichlorobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(-
trifluoromethyl)phenyl)benzamide,
2,6-difluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phe-
nylcarbamoyl)phenyl)-N-methylbenzamide,
3-(2-chloro-4-fluorobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)benzamide,
N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-N-methylbenzamide,
3-benzamido-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)b-
enzamide,
2-chloro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)nicotinamide,
6-chloro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)nicotinamide,
3-cyano-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcar-
bamoyl)phenyl)benzamide,
3-(4-cyanobenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenyl)benzamide,
2-fluoro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)benzamide,
3-fluoro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)benzamide,
3-(4-fluorobenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethy-
l)phenyl)benzamide,
2,6-difluoro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phen-
ylcarbamoyl)phenyl)benzamide,
N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)p-
henyl)-N-methylbenzamide,
2-chloro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)-N-methylnicotinamide,
3-cyano-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcar-
bamoyl)phenyl)-N-methylbenzamide,
4-cyano-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcar-
bamoyl)phenyl)-N-methylbenzamide,
[0068]
3-fluoro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)ph-
enylcarbamoyl)phenyl)-N-methylbenzamide,
4-fluoro-N-(3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylca-
rbamoyl)phenyl)-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-2-fluorophenyl)-N-methylisonicotinamide,
343-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
-2-fluorophenyl)(methyl)carbamoyl)pyridine 1-oxide,
4-((3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoy-
l)-2-fluorophenyl)(methyl)carbamoyl)pyridine 1-oxide,
2-chloro-4-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2-chloronicotinamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyanob-
enzamido)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2-fluorobenzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-fluoro-
benzamido)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-6-chloronicotinamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyanob-
enzamido)benzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-fluoro-
benzamido)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2,6-difluorobenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2-chloro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-3-cyano-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-3-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-6-chloro-N-methylnicotinamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-4-cyano-N-methylbenzamide,
[0069]
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarb-
amoyl)phenyl)-4-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
phenyl)-2,6-difluoro-N-methylbenzamide,
6-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)nicotinamide,
3-(3-cyanobenzamido)-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(triflu-
oromethyl)phenyl)benzamide,
3-(4-cyanobenzamido)-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(triflu-
oromethyl)phenyl)benzamide,
2-fluoro-3-(2-fluorobenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
2-fluoro-3-(3-fluorobenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
2-fluoro-3-(4-fluorobenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifl-
uoromethyl)phenyl)benzamide,
3-(2,6-difluorobenzamido)-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(t-
rifluoromethyl)phenyl)benzamide,
N-(3-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)-
-2-fluorophenyl)-6-chloronicotinamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(3-cyanob-
enzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyanob-
enzamido)-2-fluorobenzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3--
(2-fluorobenzamido)benzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3--
(3-fluorobenzamido)benzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3--
(4-fluorobenzamido)benzamide,
N-(2-bromo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(2,6-difl-
uorobenzamido)-2-fluorobenzamide,
2-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)-N-methylnicotinamide,
6-chloro-N-(2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)-N-methylnicotinamide,
3-(3-cyano-N-methylbenzamido)-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)--
6-(trifluoromethyl)phenyl)benzamide,
2-fluoro-N-(2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)-N-methylbenzamide,
[0070]
2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-4-(perfluorobutan-
-2-yl)-6-(trifluoromethyl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamido)-N-(2-iodo-4-(perfluorobutan-2-yl)-
-6-(trifluoromethyl)phenyl)benzamide,
2-chloro-4,5-difluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluorom-
ethyl)phenylcarbamoyl)phenyl)benzamide,
2-chloro-4-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethy-
l)phenylcarbamoyl)phenyl)-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-chloro-4-fluorobenzamide,
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)benzamide,
3-(2-chlorobenzamido)-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trif-
luoromethyl)phenyl)benzamide,
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-N-methylbenzamide,
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)phenyl)-2-chlorobenzamide,
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)-4-nitrobenzamide,
N-(2-fluoro-3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoro
methyl)phenylcarbamoyl)phenyl)-N-methylnicotinamide,
3-(2-fluoro-3-(2-iodo-4-(perfluoro
propan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl)phenyl)(methyl)carbamoyl)-
pyridine 1-oxide,
4-bromo-2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)benzamide,
2-bromo-4-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoro
methyl)phenylcarbamoyl)phenyl)benzamide,
2-bromo-4-fluoro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl-
)phenylcarbamoyl)phenyl)benzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)-N-methylbenzamide,
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-N-
-methy 1-3-(N-methylbenzamido)benzamide, or
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro--
3-(N-methylbenzamido)benzamide.
[0071] <12> The amide derivative according to <2>,
wherein in Formula (7), at least one of X represents a chlorine
atom, a bromine atom, an iodine atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9 halocycloalkyl
group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6
alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a
C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6
haloalkenyloxy group, a C2-C6 alkynyloxy group, a C2-C6
haloalkynyloxy group, a C3-C9 cycloalkoxy group, a C3-C9
halocycloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylsulfonyloxy group, a C1-C6
haloalkylsulfonyloxy group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C3-C7 alkenylcarbonyl group, a C3-C7
haloalkenylcarbonyl group, a C3-C7 alkynylcarbonyl group, a C3-C7
haloalkynylcarbonyl group, a C4-C10 cycloalkylcarbonyl group, a
C4-C10 halocycloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy
group, a C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group, a
C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a
C3-C7 alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl
group, a C3-C7 alkynyloxycarbonyl group, a C3-C7 halo
alkynyloxycarbonyl group, a C4-C10 cycloalkyloxycarbonyl group, a
C4-C10 halocycloalkyloxycarbonyl group, a C2-C7 alkylcarbonylamino
group, a C2-C7 haloalkylcarbonylamino group, a C2-C7
alkoxycarbonylamino group, a C2-C7 haloalkoxycarbonylamino group, a
C2-C7 alkoxycarbonyloxy group, a C2-C7 haloalkoxycarbonyloxy group,
an arylcarbonylamino group, an amino group, a carbamoyl group, a
cyano group, a hydroxy group, pentafluorosulfanyl group, a C1-C6
alkylamino group, a C1-C6 haloalkylamino group, a C2-C6
alkenylamino group, a C2-C6 haloalkenylamino group, a C2-C6
alkynylamino group, a C2-C6 haloalkynylamino group, a C3-C9
cycloalkylamino group, a C3-C9 halocycloalkylamino group, a C2-C7
alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl group, a
C3-C7 alkenylaminocarbonyl group, a C3-C7 haloalkenylaminocarbonyl
group, a C3-C7 alkynylaminocarbonyl group, a C3-C7
haloalkynylaminocarbonyl group, a C4-C10 cycloalkylaminocarbonyl
group, a C4-C10 halocycloalkylaminocarbonyl group, a phenyl group,
or a heterocyclic group, and when there are plural X's, each X may
be the same as or different from an other. Y.sub.1 represents a
halogen atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group.
Y.sub.5 represents a C1-C6 haloalkoxy group, or C1-C3 haloalkyl
group.
[0072] <13> The amide derivative according to <12>,
wherein in Formula (7), Y.sub.3 represents a C2-C4 perfluoroalkyl
group.
[0073] <14> The amide derivative according to <13>,
wherein in Formula (7), Y.sub.1 represents a halogen atom or a
C1-C3 haloalkyl group, and Y.sub.5 represents a C1-C3 haloalkyl
group.
[0074] <15> The amide derivative according to <14>,
wherein in Formula (7), Y.sub.2 and Y.sub.4 represent a hydrogen
atom.
[0075] <16> The amide derivative according to <15>,
wherein in Formula (7), X.sub.1 to X.sub.4 each independently
represents a hydrogen atom, a halogen atom, or a cyano group.
[0076] <17> The amide derivative according to <1>,
which is represented by the following Formula (9):
##STR00010##
[0077] Wherein, in Formula (9), n represents 4, and X, Y.sub.1 to
Y.sub.5, Q.sub.2, G.sub.1 to G.sub.3, R.sub.1, and R.sub.2 have the
same definitions as X, Y.sub.1 to Y.sub.5, Q.sub.2, G.sub.1 to
G.sub.3, R.sub.1, and R.sub.2, respectively, in Formula (1).
[0078] <18> The amide derivative according to <17>,
wherein in Formula (9), Y.sub.1 represents a halogen atom, a C1-C6
haloalkoxy group, or a C1-C3 haloalkyl group, and Y.sub.5 is a
C1-C6 haloalkoxy group or a C1-C3 haloalkyl group.
[0079] <19> The amide derivative according to <18>,
wherein in Formula (9), Y.sub.3 represents a C2-C4 perfluoroalkyl
group.
[0080] <20> The amide derivative according to <19>,
wherein in Formula (9), Y.sub.1 and Y.sub.5 represent halogen atoms
or C1-C3 haloalkyl groups, and either Y.sub.1 or Y.sub.5 represent
a C1-C3 haloalkyl group.
[0081] <21> The amide derivative according to <20>,
wherein in Formula (9), Y.sub.2 and Y.sub.4 represent hydrogen
atoms.
[0082] <22> The amide derivative according to <21>,
wherein in Formula (9), X.sub.1 to X.sub.4 each independently
represents a hydrogen atom, a halogen atom, or a cyano group.
[0083] <23> The amide derivative according to <1>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyridine,
pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine,
pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds.
[0084] <24> The amide derivative according to <23>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyridine,
in combination with A and two carbon atoms to which A bonds, and
when T is --C(=G.sub.1)-Q.sub.1, Y.sub.1 and Y.sub.5 each
independently represents a halogen atom or a C1-C3 haloalkyl
group.
[0085] <25> The amide derivative according to <23>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyrrole,
pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole,
furan, thiophene, oxadiazole, thiodiazole, or trizole, in
combination with A and two carbon atoms to which A bonds, and in a
case where T represents --C(=G.sub.1)-Q.sub.1, R.sub.1 represents
an oxygen atom, a halogen atom, a hydroxy group, a nitro group, a
nitroso group, a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, an amino group, a C1-C6 alkyl group which may
have a substituent, a C1-C6 haloalkyl group which may have a
substituent, a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl
group, a C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a
benzenesulfonyl group, a benzylsulfonyl group, a benzyl group, or
--C(.dbd.O)C(.dbd.O)R.sub.7 (wherein R.sub.7 represents a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a
C1-C6 haloalkoxy group).
[0086] <26> The amide derivative according to <23>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyrrole,
pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole,
furan, thiophene, oxadiazole, thiodiazole, or trizole, in
combination with A and two carbon atoms to which A bonds, and in a
case where T represents --C(=G.sub.1)-Q.sub.1, R.sub.2 represents
an oxygen atom, a halogen atom, a hydroxy group, a nitro group, a
nitroso group, a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, an amino group, a C1-C6 alkyl group which may
have a substituent, a C1-C6 haloalkyl group which may have a
substituent, a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl
group, a C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a
benzenesulfonyl group, a benzylsulfonyl group, a benzyl group, or
--C(.dbd.O)C(.dbd.O)R.sub.7 (wherein R.sub.7 represents a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a
C1-C6 haloalkoxy group).
[0087] <27> The amide derivative according to any one of
<23> to <26>, wherein in Formula (1), Y.sub.3
represents a C2-C4 perfluoroalkyl group.
[0088] <28> The amide derivative according to <27>,
wherein in Formula (1), Y.sub.1 and Y.sub.5 each independently
represent a halogen atom or a C1-C3 haloalkyl group, and either
Y.sub.1 or Y.sub.5 represent a C1-C3 haloalkyl group.
[0089] <29> The amide derivative according to <28>,
wherein in Formula (1), Y.sub.2 and Y.sub.4 represent hydrogen
atoms.
[0090] <30> The amide derivative according to <29>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyridine,
pyridine-N-oxide, pyrrole, thiazole, furan, or thiophene, in
combination with A and two carbon atoms to which A bonds.
[0091] <31> The amide derivative according to <29>,
wherein in Formula (1), K represents a non-metal atom group
necessary for forming a cyclic linking group derived from pyridine,
pyridine-N-oxide, or thiazole, in combination with A and two carbon
atoms to which A bonds.
[0092] <32> The amide derivative according to <16>,
wherein in Formula (7), G.sub.1 and G.sub.3 represent oxygen
atoms.
[0093] <33> The amide derivative according to <22>,
wherein in Formula (9), G.sub.1, G.sub.2, and G.sub.3 represent
oxygen atoms.
[0094] <34> The amide derivative according to <31>,
wherein in Formula (1), G.sub.1, G.sub.2, and G.sub.3 represent
oxygen atoms.
[0095] <35> A pest control agent comprising at least one
amide derivative according to any one of <1> to <34> as
an active ingredient.
[0096] <36> An agricultural chemical comprising at least one
amide derivative according to any one of <1> to <34> as
an active ingredient.
[0097] <37> A pesticide comprising at least one amide
derivative according to any one of <1> to <34> as an
active ingredient.
[0098] <38> A pest controlling method, comprising applying a
chemical agent according to any one of <35> to
<37>.
[0099] <39> A compound represented by the following Formula
(56):
##STR00011##
[0100] Wherein, wherein Y.sub.5 represents a C1-C3 haloalkyl group,
and Y.sub.2, Y.sub.3, and Y.sub.4 represent the same definitions as
Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in <1>.
[0101] <40> A compound represented by the following Formula
(57):
##STR00012##
[0102] Wherein Y.sub.5 represents a C1-C3 haloalkyl group, and
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 represent the same
definitions as Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4,
respectively, in <1>.
[0103] <41> The compound according to <40>, wherein in
Formula (57), Y.sub.1 represents a halogen atom.
[0104] <42> A method for producing a compound represented by
the following Formula (57a) according to <41>, including
reacting a compound represented by Formula (56) according to
<39> with a halogenating agent:
##STR00013##
[0105] Wherein Y.sub.5 represents a C1-C3 haloalkyl group, Y.sub.2,
Y.sub.3, and Y.sub.4 represent the same definitions as Y.sub.2,
Y.sub.3, and Y.sub.4, respectively, in <1>, and Y.sub.1
represents a halogen atom.
[0106] <43> A compound represented by the following Formula
(60a):
##STR00014##
[0107] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>. In a case where K forms a benzene ring
together with A and two carbon atoms to which A bonds and all X's
represent hydrogen atoms, Y.sub.5 represents a C1-C3 haloalkyl
group. Further, when K forms a benzene ring together with A and two
carbon atoms to which A bonds and X's are cyano groups, Y.sub.5
represents a C1-C6 haloalkoxy group or a C1-C3 haloalkyl group.
[0108] <44> A method for producing a compound represented by
the following Formula (60a) according to <43>, comprising
reacting a compound represented by the following Formula (59) with
a compound represented by the following Formula (57b):
##STR00015##
[0109] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
A, K, X, n, and G.sub.3 have the same definitions as A, K, X, n,
and G.sub.3, respectively, in <1>.
##STR00016##
[0110] Wherein Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have
the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <1>.
##STR00017##
[0111] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>. In a case where K forms a benzene ring
together with A and two carbon atoms to which A bonds and X's
represent all hydrogen atoms, Y.sub.5 represents a C1-C3 haloalkyl
group. Further, in a case where K forms a benzene ring together
with A and two carbon atoms to which A bonds and X represents a
cyano group, Y.sub.5 represents a C1-C6 haloalkoxy group or a C1-C3
haloalkyl group.
[0112] <45> A compound represented by the following Formula
(61a):
##STR00018##
[0113] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 represent the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>. In a case where K forms a benzene ring
together with A and two carbon atoms to which A bonds and all X's
represent hydrogen atoms, Y.sub.5 represents a C1-C3 haloalkyl
group. Further, when K forms a benzene ring together with A and two
carbon atoms to which A bonds and X represents a cyano group,
Y.sub.5 represents a C1-C6 haloalkoxy group or a C1-C3 haloalkyl
group.
[0114] <46> A method for producing a compound represented by
the following Formula (61a) according to <45>, including
reacting a compound represented by Formula (60a) according to
<43> with a reducing agent:
##STR00019##
[0115] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>. In a case where K forms a benzene ring
together with A and two carbon atoms to which A bonds and all X's
represent hydrogen atoms, Y.sub.5 represents a C1-C3 haloalkyl
group. Further, when K forms a benzene ring together with A and two
carbon atoms to which A bonds and X represents a cyano group,
Y.sub.5 represents a C1-C6 haloalkoxy group or a C1-C3 haloalkyl
group.
[0116] <47> A compound represented by the following Formula
(69):
##STR00020##
[0117] Wherein T, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as T, A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0118] <48> A method for producing a compound represented by
the following Formula (69) according to <47>, including
reacting a compound represented by the following Formula (61b) with
a compound represented by the following Formula (62):
##STR00021##
[0119] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
T-LG Formula (62)
[0120] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, and the like, and
T represents the same definition as T in <1>.
##STR00022##
[0121] Wherein T, A, K, X, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 represent the same definitions as T, A, K, X,
n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0122] <49> A compound represented by the following Formula
(51a):
##STR00023##
[0123] Wherein T, R.sub.1, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as T,
R.sub.1, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in <1>.
[0124] <50> A method for producing a compound represented by
the following Formula (51b), including reacting a compound
represented by the following Formula (69) according to <47>
with a compound represented by the following Formula (64):
##STR00024##
[0125] Wherein T, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as T, A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
R.sub.1-LG Formula (64)
[0126] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like,
R.sub.1 represents a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, a C1-C6 alkyl group which may have a
substituent, a C1-C6 haloalkyl group which may have a substituent,
a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a
C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7 (wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group.
##STR00025##
[0127] Wherein R.sub.1 represents the same definition as R.sub.1 in
Formula (64), and T, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as T, A, K,
X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0128] <51> A compound represented by the following Formula
(57c):
##STR00026##
[0129] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents an oxygen atom, a halogen
atom, a hydroxy group, a nitro group, a nitroso group, a
trimethylsilyl group, a t-butyldimethylsilyl group, a cyano group,
an amino group, a C1-C6 alkyl group which may have a substituent, a
C1-C6 haloalkyl group which may have a substituent, a C2-C7
alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a C2-C6
alkenyl group which may have a substituent, a C2-C6 haloalkenyl
group which may have a substituent, a C2-C6 alkynyl group which may
have a substituent, a C2-C6 haloalkynyl group which may have a
substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a
benzenesulfonyl group, a benzylsulfonyl group, a benzyl group, or
--C(.dbd.O)C(.dbd.O)R.sub.7 (wherein R.sub.7 represents a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a
C1-C6 haloalkoxy group), and Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <1>.
[0130] <52> A method for producing a compound represented by
the following Formula (57m), including reacting a compound
represented by the following Formula (57k) with a compound
represented by the following Formula (66):
##STR00027##
[0131] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, and Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <1>.
R.sub.2-LG Formula (66)
[0132] Wherein, LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like,
R.sub.2 represents a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, a C1-C6 alkyl group which may have a
substituent, a C1-C6 haloalkyl group which may have a substituent,
a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a
C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7, wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group.
##STR00028##
[0133] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents the same definition as
R.sub.2 in Formula (66), and Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <1>.
[0134] <53> A method for producing a compound represented by
the following Formula (57n), including reacting a compound
represented by the following Formula (57k) according to <52>
with an aldehyde:
##STR00029##
[0135] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, and Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <1>.
##STR00030##
[0136] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents a C1-C6 alkyl group which
may have a substituent, a C1-C6 haloalkyl group which may have a
substituent, or a benzyl group, and Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4 have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <1>.
[0137] <54> A compound represented by the following Formula
(60):
##STR00031##
[0138] Wherein R.sub.2 represents the same definition as R.sub.2 in
<51>, and A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0139] <55> A method for producing a compound represented by
the following Formula (60e), including reacting a compound
represented by the following Formula (60f) with a compound
represented by the following Formula (66) according to
<52>:
##STR00032##
[0140] Wherein A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
R.sub.2-LG Formula (66)
[0141] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like,
R.sub.2 represents a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, a C1-C6 alkyl group which may have a
substituent, a C1-C6 haloalkyl group which may have a substituent,
a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a
C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7 (wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group.
##STR00033##
[0142] Wherein R.sub.2 has the same definition as R.sub.2 in
Formula (66), and A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0143] <56> A method for producing a compound represented by
the following Formula (60) according to <54>; including
reacting a compound represented by the following Formula (57d) with
a compound represented by the following Formula (59) according to
<44>:
##STR00034##
[0144] Wherein R.sub.2 has the same definition as R.sub.2 in
<51>, and Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in <1>.
##STR00035##
[0145] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
A, K, X, n, and G.sub.3 have the same definitions as A, K, X, n,
and G.sub.3, respectively, in <1>.
##STR00036##
[0146] Wherein R.sub.2 has the same definition as R.sub.2 in
<51>, and A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0147] <57> A compound represented by the following Formula
(61):
##STR00037##
[0148] Wherein R.sub.2 has the same definition as R.sub.2 in
<51>, and A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0149] <58> A method for producing a compound represented by
the following Formula (61) according to <57>, including the
compound represented by Formula (60) according to <54> in the
presence of a reducing agent:
##STR00038##
[0150] Wherein R.sub.2 has the same definition as R.sub.2 in
<51>, and A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as A, K, X, n,
G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0151] <59> A compound represented by the following Formula
(63):
##STR00039##
[0152] Wherein T, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as T,
R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in <1>.
[0153] <60> A method for producing a compound represented by
the following Formula (63) according to <59>, including
reacting a compound represented by the following Formula (61e) with
a compound represented by the following Formula (62) according to
<48>:
##STR00040##
[0154] Wherein R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2,
A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <1>.
T-LG Formula (62)
[0155] (wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
T has the same definition as T in <1>.
##STR00041##
[0156] Wherein T, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 represent the same definitions as T,
R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in <1>.
[0157] <61> A method for producing a compound represented by
the following Formula (1b), including reacting a compound
represented by the following Formula (63) according to <59>
with a compound represented by the following Formula (64) according
to <50>:
##STR00042##
[0158] Wherein T, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as T,
R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in <1>.
R.sub.1-LG Formula ((64)
[0159] Wherein, LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like,
R.sub.1 represents a trimethylsilyl group, a t-butyldimethylsilyl
group, a cyano group, a C1-C6 alkyl group which may have a
substituent, a C1-C6 haloalkyl group which may have a substituent,
a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a
C2-C6 alkenyl group which may have a substituent, a C2-C6
haloalkenyl group which may have a substituent, a C2-C6 alkynyl
group which may have a substituent, a C2-C6 haloalkynyl group which
may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C3-C7 alkenyloxycarbonyl group, a C3-C7
haloalkenyloxycarbonyl group, a C3-C7 alkynyloxycarbonyl group, a
C3-C7 haloalkynyloxycarbonyl group, a phenoxycarbonyl group, a
C2-C7 alkylaminocarbonyl group, a C2-C7 haloalkylaminocarbonyl
group, a C2-C7 alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy
group, a benzoyl group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7, wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group.
##STR00043##
[0160] Wherein R.sub.1 has the same definition as R.sub.1 in
Formula (64), and R.sub.2, A, K, X, n, G.sub.3, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2, A, K, X,
n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <1>.
[0161] <62> A compound represented by the following Formula
(65a):
##STR00044##
[0162] Wherein R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <1>. In a case where K
forms a benzene ring together with A and two carbon atoms to which
A bonds, all X's represent hydrogen atoms, and R.sub.2 represents a
hydrogen atom, Y.sub.5 is a C1-C3 haloalkyl group. Further, in a
case where K forms a benzene ring together with A and two carbon
atoms to which A bonds, X represents a cyano group, and R.sub.1 and
R.sub.2 represent hydrogen atoms, and Y.sub.5 represents a C1-C6
haloalkoxy group or a C1-C3 haloalkyl group.
[0163] <63> A method for producing a compound represented by
the following Formula (65c), including reacting a compound
represented by the following Formula (61e) according to <60>
with an aldehyde:
##STR00045##
[0164] Wherein R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2,
A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <1>.
##STR00046##
[0165] Wherein R.sub.1 represents a C1-C6 alkyl group which may
have a substituent, a C1-C6 haloalkyl group which may have a
substituent, or a benzyl group, and R.sub.2, A, K, X, n, G.sub.3,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 represent the same
definitions as R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in <1>. In a
case where K forms a benzene ring together with A and two carbon
atoms to which A bonds, all X's represent hydrogen atoms, and
R.sub.2 represents a hydrogen atom, Y.sub.5 represents a C1-C3
haloalkyl group.
[0166] <64> A method for producing a compound represented by
the following Formula (1), including reacting a compound
represented by the following Formula (65b) with a compound
represented by the following Formula (62) according to
<48>:
##STR00047##
[0167] Wherein R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <1>.
T-LG Formula (62)
[0168] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
T has the same definition as T in <1>.
##STR00048##
[0169] <65> A compound represented by the following Formula
(68):
##STR00049##
[0170] Wherein Xa represents a chlorine atom, a bromine atom, or an
iodine atom, and R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2,
A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <23>.
[0171] <66> A method for producing a compound represented by
the following Formula (68) according to <65>, including
reacting a compound represented by the following Formula (57j) with
a compound represented by the following Formula (67):
##STR00050##
[0172] Wherein R.sub.2, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as R.sub.2, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in <1>.
##STR00051##
[0173] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, Xa
represents a chlorine atom, a bromine atom, or an iodine atom, and
A, K, X, n, and G.sub.3 have the same definitions as A, K, X, n,
and G.sub.3, respectively, in <23>.
##STR00052##
[0174] Wherein Xa represents a chlorine atom, a bromine atom, or an
iodine atom, and R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2,
A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <23>.
[0175] <67> A method for producing a compound represented by
the following Formula (65d), including reacting a compound
represented by the following Formula (68) according to <65>
with an aminating agent:
##STR00053##
[0176] Wherein Xa represents a chlorine atom, a bromine atom, or an
iodine atom, and R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2,
A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <23>.
##STR00054##
[0177] Wherein R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
R.sub.1, R.sub.2, A, K, X, n, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <23>.
[0178] <68> A compound represented by the following Formula
(70):
##STR00055##
[0179] Wherein Xb represents a chlorine atom, a bromine atom, or an
iodine atom, and R.sub.2, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definition as, respectively, in
<1>.
[0180] <69> A compound represented by the following Formula
(72):
##STR00056##
[0181] Wherein R.sub.2, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2, G.sub.3,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<1>.
[0182] <70> A method for producing a compound represented by
the following Formula (72) according to <69>, including
reacting a compound represented by Formula (70) according to
<68> with a fluorinating agent:
##STR00057##
[0183] Wherein R.sub.2, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2, G.sub.3,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<1>.
[0184] <71> A compound represented by the following Formula
(73):
##STR00058##
[0185] Wherein Xc represents a halogen atom, and R.sub.2, G.sub.3,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as R.sub.2, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <1>.
[0186] <72> A compound represented by the following Formula
(75):
##STR00059##
[0187] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, and R.sub.2, G.sub.3, Y.sub.1, Y.sub.2,
Y.sub.3, and Y.sub.4 have the same definitions as R.sub.2, G.sub.3,
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in
<1>.
[0188] <73> A method for producing a compound represented by
the following Formula (75) according to <72>, including
reacting a compound represented by Formula (73) according to
<71>, in which Y.sub.5 is a C1-C6 haloalkoxy group or a C1-C3
haloalkyl group, with a cyanating agent:
##STR00060##
[0189] Wherein Y.sub.5 represents a C1-C6 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
and Y.sub.4 have the same definitions as R.sub.2, G.sub.3, Y.sub.1,
Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in <1>.
[0190] <74> A compound represented by the following Formula
(56a):
##STR00061##
[0191] Wherein Y.sub.5 represents a C1-C3 haloalkyl group, and
Y.sub.2, Y.sub.3, and Y.sub.4 have the same definitions as Y.sub.2,
Y.sub.3, and Y.sub.4, respectively, in <3>.
[0192] <75> A compound represented by the following Formula
(57e):
##STR00062##
[0193] Wherein Y.sub.5 represents a C1-C3 haloalkyl group, and
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 have the same definitions as
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 according to <3>.
[0194] <76> The compound according to <75>, wherein in
Formula (57e), Y.sub.1 is a halogen atom.
[0195] <77> A method for producing a compound represented by
the following Formula (571) according to <76>, including
reacting a compound represented by Formula (56a) according to
<74> with a halogenating agent:
##STR00063##
[0196] Wherein Y.sub.5 represents a C1-C3 haloalkyl group, Y.sub.2,
Y.sub.3, and Y.sub.4 represent the same definitions as Y.sub.2,
Y.sub.3, and Y.sub.4, respectively, in <3>, and Y.sub.1
represents a halogen atom.
[0197] <78> A compound represented by the following Formula
(60b):
##STR00064##
[0198] Wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <3>. In a case where
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 represent all hydrogen
atoms, Y.sub.5 represents a C1-C3 haloalkyl group, and in a case
where X.sub.2 represents a cyano group, and X.sub.1, X.sub.3, and
X.sub.4 represent hydrogen atoms, Y.sub.5 represents a C1-C3
haloalkoxy group or a C1-C3 haloalkyl group.
[0199] <79> A method for producing a compound represented by
the following Formula (60b) according to <78>, including
reacting a compound represented by the following Formula (59a) with
a compound represented by the following Formula (57g):
##STR00065##
[0200] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 in <3>.
##STR00066##
[0201] Wherein Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have
the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <3>.
##STR00067##
[0202] Wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <3>. In a case where
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 represent all hydrogen
atoms, Y.sub.5 represents a C1-C3 haloalkyl group, and in a case
where X.sub.2 represents a cyano group, and X.sub.1, X.sub.3, and
X.sub.1 represent hydrogen atoms, Y.sub.5 represents a C1-C3
haloalkoxy group or a C1-C3 haloalkyl group.
[0203] <80> A compound represented by the following Formula
(61f):
##STR00068##
[0204] Wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <3>. In a case where
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 represent all hydrogen
atoms, Y.sub.5 represents a C1-C3 haloalkyl group, and in a case
where X.sub.2 represents a cyano group, and X.sub.1, X.sub.3, and
X.sub.4 represent hydrogen atoms, Y.sub.5 represents a C1-C3
haloalkoxy group or a C1-C3 haloalkyl group.
[0205] <81> A method for producing a compound represented by
the following Formula (610 according to <80>, including
reacting a compound represented by a compound represented by
Formula (60b) according to <78> in the presence of a reducing
agent:
##STR00069##
[0206] Wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <3>. In a case where
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 represent all hydrogen
atoms, Y.sub.5 represents a C1-C3 haloalkyl group, and in a case
where X.sub.2 represents a cyano group, and X.sub.1, X.sub.3, and
X.sub.4 represent hydrogen atoms, Y.sub.5 represents a C1-C3
haloalkoxy group or a C1-C3 haloalkyl group.
[0207] <82> A compound represented by the following Formula
(69a):
##STR00070##
[0208] Wherein Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
[0209] <83> A method for producing a compound represented by
the following Formula (69a) according to <82>, including
reacting a compound represented by the following Formula (61c) with
a compound represented by the following Formula (62a):
##STR00071##
[0210] Wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 represent the same
definitions as X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
##STR00072##
[0211] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
Q.sub.1 represents the same definition as Q.sub.1 in <3>.
##STR00073##
[0212] Wherein Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 represent the same
definitions as Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
[0213] <84> A compound represented by the following Formula
(53a):
##STR00074##
[0214] Wherein Q.sub.1, R.sub.1, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as Q.sub.1, R.sub.1, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0215] <85> A method for producing a compound represented by
the following Formula (53b), including reacting a compound
represented by the following Formula (69a) according to <82>
with a compound represented by the following Formula (64a):
##STR00075##
[0216] Wherein Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
R.sub.1-LG Formula (64a)
[0217] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
R.sub.1 represents a C1-C3 alkyl group.
##STR00076##
[0218] Wherein R.sub.1 has the same definition as R.sub.1 in
Formula (64a), and Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as Q.sub.1, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5/respectively, in
<3>.
[0219] <86> A compound represented by the following Formula
(57h):
##STR00077##
[0220] Wherein Y.sub.5 represents a C1-C3 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents a C1-C3 alkyl group, and
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 have the same definitions as
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in
<3>.
[0221] <87> A method for producing a compound represented by
the following Formula (57h) according to <86>, including
reacting a compound represented by the following Formula (571) with
a compound represented by the following Formula (66a):
##STR00078##
[0222] Wherein Y.sub.5 represents a C1-C3 haloalkoxy group or a
C1-C3 haloalkyl group, and Y.sub.2, Y.sub.3, and Y.sub.4 have the
same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4,
respectively, in <3>.
R.sub.2-LG Formula (66a)
[0223] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
R.sub.2 represents a C1-C3 alkyl group.
##STR00079##
[0224] Wherein Y.sub.5 represents a C1-C3 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents a C1-C3 alkyl group, and
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 have the same definitions as
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in
<3>.
[0225] <88> A method for producing a compound represented by
the following Formula (57h) according to <86>, including
reacting a compound represented by the following Formula (571)
according to <87> with an aldehyde:
##STR00080##
[0226] Wherein Y.sub.5 represents a C1-C3 haloalkoxy group or a
C1-C3 haloalkyl group, and Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4
have the same definitions as Y.sub.1, Y.sub.2, Y.sub.3, and
Y.sub.4, respectively, in <3>.
##STR00081##
[0227] Wherein Y.sub.5 represents a C1-C3 haloalkoxy group or a
C1-C3 haloalkyl group, R.sub.2 represents a C1-C3 alkyl group, and
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 have the same definitions as
Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4, respectively, in
<3>.
[0228] <89> A compound represented by the following Formula
(60c):
##STR00082##
[0229] Wherein R.sub.2 represents a C1-C3 alkyl group, and X.sub.1,
X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0230] <90> A method for producing a compound represented by
the following Formula (60c) according to <89>, including
reacting a compound represented by the following Formula (60d) with
a compound represented by the following Formula (66a) according to
<87>:
##STR00083##
[0231] Wherein. X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5, respectively, in <3>.
R.sub.2-LG Formula (66a)
[0232] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
R.sub.2 represents a C1-C3 alkyl group.
##STR00084##
[0233] (Wherein R.sub.2 represents a C1-C3 alkyl group, and
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as X.sub.1, X.sub.2,
X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0234] <91> A method for producing a compound represented by
the following Formula (60c) according to <89>, including
reacting a compound represented by the following Formula (57i) with
a compound represented by the following Formula (59a) according to
<79>:
##STR00085##
[0235] Wherein R.sub.2 represents a C1-C3 alkyl group, and Y.sub.1,
Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same definitions as
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
##STR00086##
[0236] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like,
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 have the same definitions as
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 in <3>.
##STR00087##
[0237] Wherein R.sub.2 represents a C1-C3 alkyl group, and X.sub.1,
X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0238] <92> A compound represented by the following Formula
(61g):
##STR00088##
[0239] Wherein R.sub.2 represents a C1-C3 alkyl group, and X.sub.1,
X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0240] <93> A method for producing a compound represented by
the following Formula (61g) according to <92>, including
reacting a compound represented by Formula (60c) according to
<89> in the presence of a reducing agent:
##STR00089##
[0241] Wherein R.sub.2 represents a C1-C3 alkyl group, and X.sub.1,
X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0242] <94> A compound represented by the following Formula
(63c):
##STR00090##
[0243] Wherein Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0244] <95> A method for producing a compound represented by
the following Formula (63c) according to <94>, including
reacting a compound represented by the following Formula (61d) with
a compound represented by the following Formula (62a) according to
<83>:
##STR00091##
[0245] Wherein R.sub.2, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as R.sub.2, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
##STR00092##
[0246] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
Q.sub.1 has the same definition as Q.sub.1 in <3>.
##STR00093##
[0247] Wherein Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0248] <96> A method for producing a compound represented by
the following Formula (3a), including reacting a compound
represented by the following Formula (63c) according to <94>
with a compound represented by the following Formula (64a)
according to <85>:
##STR00094##
[0249] Wherein Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
R.sub.1-LG Formula (64a)
[0250] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
R.sub.1 represents a C1-C3 alkyl group.
##STR00095##
[0251] Wherein R.sub.1 has the same definition as R.sub.1 in
Formula (64a), and Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as Q.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
[0252] <97> A compound represented by the following Formula
(65e):
##STR00096##
[0253] Wherein R.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as R.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>. In a case where X.sub.1, X.sub.2,
X.sub.3, and X.sub.4, represent all hydrogen atoms, and R.sub.2
represents a hydrogen atom, Y.sub.5 represents a C1-C3 haloalkyl
group, and in a case where X.sub.2 represents a cyano group,
X.sub.1, X.sub.3, and X.sub.4 represent hydrogen atoms, and R.sub.1
and R.sub.2 represent hydrogen atoms, Y.sub.5 represents a C1-C3
haloalkoxy group or a C1-C3 haloalkyl group.
[0254] <98> A method for producing a compound represented by
the following Formula (65f), including reacting a compound
represented by the following Formula (61d) with an aldehyde:
##STR00097##
[0255] Wherein R.sub.2, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the same
definitions as R.sub.2, X.sub.1, X.sub.2, X.sub.3, X.sub.4,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in
<3>.
##STR00098##
[0256] Wherein R.sub.1 represents a C1-C3 alkyl group, and R.sub.2,
X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 have the same definitions as R.sub.2, X.sub.1,
X.sub.2, X.sub.3, X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5, respectively, in <3>. In a case where X.sub.1,
X.sub.2, X.sub.3, and X.sub.4 represent all hydrogen atoms, and
R.sub.2 represents a hydrogen atom, Y.sub.5 represents a C1-C3
haloalkyl group.
[0257] <99> A method for producing a compound represented by
the following Formula (3) according to <3>, including
reacting a compound represented by the following Formula (65g) with
a compound represented by the following Formula (62a) according to
<83>:
##STR00099##
[0258] Wherein R.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 have the
same definitions as R.sub.1, R.sub.2, X.sub.1, X.sub.2, X.sub.3,
X.sub.4, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in <3>.
##STR00100##
[0259] Wherein LG represents a functional group having a leaving
ability, such as a halogen atom, a hydroxy group, or the like, and
Q.sub.1 has the same definition as Q.sub.1 in <3>.
##STR00101##
[0260] <100> A compound represented by the following Formula
(70a):
##STR00102##
[0261] Wherein Xb represents a chlorine atom, a bromine atom, or an
iodine atom, and R.sub.2, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as R.sub.2, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in <3>.
[0262] <101> A compound represented by the following Formula
(72a):
##STR00103##
[0263] Wherein R.sub.2, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as R.sub.2, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in <3>.
[0264] <102> A method for producing a compound represented by
the following Formula (72a) according to <101>, including
reacting a compound represented by Formula (70a) according to
<100> with a fluorinating agent:
##STR00104##
[0265] Wherein R.sub.2, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and
Y.sub.5 have the same definitions as R.sub.2, Y.sub.1, Y.sub.2,
Y.sub.3, Y.sub.4, and Y.sub.5, respectively, in <3>.
[0266] <103> A composition for controlling a pest comprising
as an active ingredient at least one amide derivative represented
by the following Formula (A1):
##STR00105##
[0267] Wherein, in Formula (A1), Q.sub.1 represents a phenyl group
or a phenyl group substituted with a halogen atom; X.sub.1
represents a fluorine atom; X.sub.2, X.sub.3, and X.sub.4 are each
a hydrogen atom; R.sub.1 represents a hydrogen atom or a C1-C3
alkyl group; R.sub.2 is a hydrogen atom; Y.sub.1 and Y.sub.5 each
independently represent a halogen atom or a C1-C3 haloalkyl group;
Y.sub.2 and Y.sub.4 each represent a hydrogen atom; and Y.sub.3
represents a heptafluoroisopropyl group.
[0268] <104> The composition according to <103>,
wherein the pest is an animal parasite.
[0269] <105> The composition according to <104>,
wherein in Formula (A1), Q.sub.1 represents a phenyl group or a
phenyl group substituted with a single fluorine atom; R.sub.1
represents a hydrogen atom or a methyl group; and Y.sub.1 and
Y.sub.5 each independently represent a bromine or iodine atom or a
trifluoromethyl group.
[0270] <106> The composition according to <105>,
wherein the amide derivative represented by Formula (A1) is
2-fluoro-3-(N-methylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluor-
opropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluorobenzamide)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoro-
propan-2-yl)phenyl)benzamide, or
2-fluoro-3-(N-methylbenzamide)-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)p-
henyl)benzamide
[0271] <107> A method for exterminating animal parasites,
comprising administering to an animal the composition according to
<104> to <106>.
[0272] <108> The method according to <107>, wherein the
animal parasite is an ectoparasite.
[0273] <109> The method according to <108>, wherein the
ectoparasite is Siphonaptera pests.
[0274] <110> The method according to <108>, wherein the
ectoparasite is Acarina pests.
[0275] According to the present invention, an amide derivative
showing a pesticidal effect against a wide range of
agricultural/horticultural pests, a pest control agent containing
the amide derivative as an active ingredient, and a pest
controlling method are provided.
DETAILED DESCRIPTION OF THE INVENTION
[0276] An amide compound according to the present invention is
represented by the following Formula (1).
##STR00106##
[0277] In Formula (1), A represents a carbon atom, an oxygen atom,
a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom. K
represents a non-metal atom group necessary for forming a cyclic
linking group derived from benzene, pyridine, pyridine-N-oxide,
pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole,
imidazole, oxazole, isoxazole, thiazole, isothiazole, furan,
thiophene, oxadiazole, thiodiazole, or triazole, in combination
with A and two carbon atoms to which A bonds.
[0278] X represents a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9
halocycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6
alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a
C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylsulfonyloxy group, a C1-C6
haloalkylsulfonyloxy group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy group, a C2-C7
haloalkylcarbonyloxy group, arylcarbonyloxy group, a C2-C7
alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C2-C7
alkylcarbonylamino group, a C2-C7 haloalkylcarbonylamino group, a
C2-C7 alkoxycarbonylamino group, a C2-C7 haloalkoxycarbonylamino
group, a C2-C7 alkoxycarbonyloxy group, a C2-C7
haloalkoxycarbonyloxy group, an arylcarbonylamino group, an amino
group, a carbamoyl group, a cyano group, a hydroxy group,
pentafluorosulfanyl group, a C1-C6 alkylamino group, a C1-C6
haloalkylamino group, a C2-C6 alkenylamino group, a C2-C6
haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloalkenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, a phenyl group, or a
heterocyclic group, and when there are plural X's, each X may be
the same as or different from an other.
[0279] n represents an integer of from 0 to 4. T represents
--C(=G.sub.1)-Q.sub.1 or --C(=G.sub.1)-G.sub.2Q.sub.2. G.sub.1 and
G.sub.2 each independently represent an oxygen atom or a sulfur
atom, and Q.sub.1 and Q.sub.2 represent a hydrogen atom, a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a
C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl
group, a C3-C9 cycloalkyl group, a C3-C9 halocycloalkyl group, a
benzyl group, a phenyl group which may have a substituent, a
naphthyl group, or a heterocyclic group which may have a
substituent.
[0280] Y.sub.1 and Y.sub.5 each independently represent a halogen
atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group, Y.sub.2
and Y.sub.4 each independently represent a hydrogen atom, a halogen
atom, or a C1-C4 alkyl group, Y.sub.3 represents a C2-C5 haloalkyl
group.
[0281] Further, in Q.sub.1 and Q.sub.2, the substituent of a phenyl
group which may have a substituent and a heterocyclic group which
may have a substituent represents one or more substituent selected
from a group consisting of a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, a C3-C9
halocycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl
group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6
alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a
C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C2-C7 alkylcarbonyloxy group, a C2-C7
haloalkylcarbonyloxy group, a C1-C6 alkylsulfonyloxy group, a C1-C6
haloalkylsulfonyloxy group, a C2-C7 alkoxycarbonyl group, a C2-C7
haloalkoxycarbonyl group, a C2-C7 alkylcarbonylamino group, a C2-C7
haloalkylcarbonylamino group, a C2-C7 alkoxycarbonylamino group, a
C2-C7 haloalkoxycarbonylamino group, a C1-C6 alkylamino group, a
C1-C6 haloalkylamino group, a C2-C6 alkenylamino group, a C2-C6
haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C3-C7 alkenylaminocarbonyl
group, a C3-C7 haloalkenylaminocarbonyl group, a C3-C7
alkynylaminocarbonyl group, a C3-C7 haloalkynylaminocarbonyl group,
a C4-C10 cycloalkylaminocarbonyl group, a C4-C10
halocycloalkylaminocarbonyl group, an amino group, a carbamoyl
group, a cyano group, a nitro group, a hydroxy group,
pentafluorosulfanyl group, a phenyl group which may have a
substituent, and a heterocyclic group which may have a substituent,
and when there are two or more substituents, each substituent may
be the same as or different from each other.
[0282] Moreover, the heterocyclic group in X, Q.sub.1, and Q.sub.2
represent a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyrazinyl group, a pyridazyl group, furyl group, thienyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group.
[0283] G.sub.3 represents an oxygen atom or a sulfur atom.
[0284] R.sub.1 and R.sub.2 each independently represent a hydrogen
atom, an oxygen atom, a halogen atom, a hydroxy group, a nitro
group, a nitroso group, a trimethylsilyl group, a
t-butyldimethylsilyl group, a cyano group, an amino group, a C1-C6
alkyl group which may have a substituent, a C1-C6 haloalkyl group
which may have a substituent, a C2-C7 alkylcarbonyl group, a C2-C7
haloalkylcarbonyl group, a C2-C6 alkenyl group which may have a
substituent, a C2-C6 haloalkenyl group which may have a
substituent, a C2-C6 alkynyl group which may have a substituent, a
C2-C6 haloalkynyl group which may have a substituent, a C2-C7
alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C3-C7
alkenyloxycarbonyl group, a C3-C7 haloalkenyloxycarbonyl group, a
C3-C7 alkynyloxycarbonyl group, a C3-C7 haloalkynyloxycarbonyl
group, a phenoxycarbonyl group, a C2-C7 alkylaminocarbonyl group, a
C2-C7 haloalkylaminocarbonyl group, a C2-C7 alkylcarbonyloxy group,
a C2-C7 haloalkylcarbonyloxy group, a benzoyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a benzenesulfonyl group, a benzylsulfonyl
group, a benzyl group, or --C(.dbd.O)C(.dbd.O)R.sub.7 (wherein
R.sub.7 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C1-C6 alkoxy group, or a C1-C6 haloalkoxy group).
[0285] However the amide derivative represented by Formula (1) is
not one of (A) to (I):
[0286] (A) A case where in Formula (1), K represents a non-metal
atom group necessary for fanning a cyclic linking group derived
from pyridine in combination with A and two carbon atoms to which A
bonds, Y.sub.1 represents a halogen atom, and Y.sub.5 represents a
C1-C6 haloalkoxy group, and T is --C(=G.sub.1)-Q.sub.1.
[0287] (B) A case where in Formula (1), K represents a non-metal
atom group necessary for forming a cyclic linking group derived
from pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds, Y.sub.1 and Y.sub.5 represent each independently a halogen
atom, and T is --C(=G.sub.1)-G.sub.2Q.sub.2.
[0288] (C) A case where in Formula (1), K represents a non-metal
atom group necessary for forming a cyclic linking group derived
from pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole,
isothiazole, furan, thiophene, oxadiazole, thiodiazole, or
triazole, in combination with A and two carbon atoms to which A
bonds, T represents --C(=G.sub.1)-Q.sub.1, Y.sub.1 is a halogen
atom, and Y.sub.5 represents a halogen atom or a haloalkoxy
group.
[0289] (D) A case where the amide derivative is an amide compound
represented by the following Formula (2):
##STR00107##
[0290] In Formula (2), Y.sub.2 to Y.sub.4, Q.sub.1, G.sub.1,
G.sub.3, R.sub.1, and R.sub.2 have the same definitions as Y.sub.2
to Y.sub.4, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and R.sub.2,
respectively, in Formula (1), Y.sub.1 represents a halogen atom,
and Y.sub.5 represents a C1-C2 haloalkoxy group.
[0291] (E) A case where in Formula (2), Y.sub.1 and Y.sub.5
represent halogen atoms, all X's represent hydrogen atoms, and
Y.sub.3 represents a C2-C3 haloalkyl group.
[0292] (F) A case where the amide derivative is an amide derivative
represented by the following Formula (3)
##STR00108##
[0293] In Formula (3), Y.sub.1 and Y.sub.5 each independently
represent a halogen atom, X.sub.1 and X.sub.3 each independently
represent a hydrogen atom or a fluorine atom, Q.sub.1 has the same
definition as Q.sub.1 in Formula (1), R.sub.1 represents a hydrogen
atom or a methyl group, and Y.sub.3 represents a C3-C4
perfluoroalkyl group.
[0294] (G) A case where the amide derivative is an amide derivative
represented by the following Formula (4):
##STR00109##
[0295] In Formula (4), X.sub.1 represents a fluorine atom, X.sub.2,
X.sub.3, and X.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5
are different from each other and represent a bromine atom or a
trifluoromethoxy group, Y.sub.2 and Y.sub.4 represent hydrogen
atoms, Y.sub.3 represents a heptafluoroisopropyl group, Q.sub.1
represents a phenyl group or a 2-chloropyridin-3-yl group, and
R.sub.1 and R.sub.2 are different from each other, and represent a
hydrogen atom or a methyl group.
[0296] Alternatively, X.sub.1 represents a fluorine atom, X.sub.2,
X.sub.3, and X.sub.4 represent hydrogen atoms, Y.sub.1 and Y.sub.5
represent bromine atoms, Y.sub.2 and Y.sub.4 represent hydrogen
atoms, Y.sub.3 represents a pentafluoroethyl group, Q.sub.1
represents a 2-fluorophenyl group, and R.sub.1 and R.sub.2 each
independently represent a hydrogen atom or a methyl group.
[0297] (H) A case where the amide derivative is an amide derivative
represented by the following Formula (5):
##STR00110##
[0298] In Formula (5), Y.sub.1 and Y.sub.5 each independently
represent a halogen atom, X.sub.1 represents a hydrogen atom or a
fluorine atom, Q.sub.2 represents a 2,2,2-trichloroethyl group or a
3,3,3-trifluoro-n-propyl group, and Y.sub.3 represents a C2-C4
haloalkyl group.
[0299] (I) A case where the amide derivative is an amide derivative
represented by the following Formula (6)
##STR00111##
[0300] In Formula (6), Y.sub.1 and Y.sub.5 each independently
represent a halogen atom, Q.sub.2 has the same definition as
Q.sub.2 in Formula (1), R.sub.1 represents a hydrogen atom or a
methyl group, and Y.sub.3 represents a C3-C4 haloalkyl group
[0301] In the aspect of a pest control activity, the amide
derivative preferably represented by the following Formula (7), and
more preferably represented by the following Formula (8).
##STR00112##
[0302] In Formula (7), X, n is 4, Y.sub.1 to Y.sub.5, Q.sub.1,
G.sub.1, G.sub.3, R.sub.1, and R.sub.2 have the same definitions as
X, Y.sub.1 to Y.sub.5, Q.sub.1, G.sub.1, G.sub.3, R.sub.1, and
R.sub.2, respectively, in Formula (1).
##STR00113##
[0303] In Formula (8), Q.sub.1 represents a phenyl group which may
have a substituent or a pyridyl group which may have a substituent.
X.sub.1, X.sub.2, X.sub.3 and X.sub.4 each independently represent
hydrogen atoms or fluorine atoms. R.sub.1 and R.sub.2 each
independently represent hydrogen atoms or C1-C3 alkyl groups.
[0304] Y.sub.1 and Y.sub.5 each independently represent halogen
atoms, C1-C3 haloalkoxyl groups, or C1-C3 haloalkyl groups, Y.sub.2
and Y.sub.4 each independently represent hydrogen atoms, halogen
atoms, C1-C4 alkyl groups, and Y.sub.3 represents a C3-C4 haloalkyl
group.
[0305] In a case where Y.sub.1 and Y.sub.5 represent halogen atoms
simultaneously, at least one of X.sub.1 and X.sub.2 represents a
fluorine atom. Further, in a case where Y.sub.1 or Y.sub.5
represents a C1-C3 haloalkoxy group, X.sub.2 represents a fluorine
atom.
[0306] The terms used in the formulae including the Formula (1) and
the like according to the present invention, have the same meanings
as described below in the definitions.
[0307] The "halogen atom" represents a fluorine atom, a chlorine
atom, a bromine atom, or an iodine atom.
[0308] The expression "Ca-Cb (wherein a and b represent an integer
of 1 or more)", for example, "C1-C3" means the number of carbon
atoms of from 1 to 3, the "C2-C6" means the number of carbon atoms
of from 2 to 6, and the "C1-C4" means the number of carbon atoms of
from 1 to 4.
[0309] "n-" means normal, "i-" means iso, "s-" means secondary, and
"t-" means tertiary.
[0310] The "C1-C3 alkyl group" in the present invention represents,
for example, a linear or branched alkyl group having from 1 to 3
carbon atoms such as methyl, ethyl, n-propyl, propyl, and the
like.
[0311] The "C1-C3 haloalkyl group" represents, for example, a
linear or branched alkyl group having from 1 to 3 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other, such as trifluoromethyl,
pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl,
2,2-difluoroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl,
2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,
2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2-propyl,
1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl,
1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n-propyl,
1,1,1,3,3,3-hexafluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl,
2,2,3,3,3-pentafluoro-n-propyl, 3-fluoro-n-propyl,
3-chloro-n-propyl, 3-bromo-n-propyl, and the like.
[0312] The "C1-C4 alkyl group" represents, for example, a linear or
branched alkyl group having from 1 to 4 carbon atoms such as
methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, and
the like.
[0313] The "C1-C3 haloalkoxy group" represents, for example, a
linear or branched alkoxy group having from 1 to 3 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other, such as trifluoromethoxy,
pentafluoroethoxy, heptafluoro-n-propyloxy,
heptafluoro-i-propyloxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy,
2,2,2-trifluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy,
2-bromoethoxy, 2-iodoethoxy, 2,2,2-trichloroethoxy,
2,2,2-tribromoethoxy, 1,3-difluoro-2-propyloxy,
1,3-dichloro-2-propyloxy, 1-chloro-3-fluoro-2-propyloxy,
1,1,1-trifluoro-2-propyloxy, 2,3,3,3-trifluoro-n-propyloxy,
1,1,1,3,3,3-hexafluoro-2-propyloxy,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyloxy,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propyloxy,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propyloxy,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propyloxy,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propyloxy,
2,2,3,3,3-pentafluoro-n-propyloxy, 3-fluoro-n-propyloxy,
3-chloro-n-propyloxy, 3-bromo-n-propyloxy, and the like.
[0314] The "C3-C4 perfluoroalkyl group" represents, for example, a
linear or branched alkyl group having from 3 to 4 carbon atoms,
that all hydrogen atoms is substituted with fluorine atoms such as
perfluoro-n-propyl, perfluoro-i-propyl, perfluoro-n-butyl,
perfluoro-1-butyl, perfluoro-s-butyl, perfluoro-t-butyl, and the
like.
[0315] The "C1 haloalkyl group" represents, for example, a methyl
group that is substituted with one or more halogen atoms which may
be the same as or different from each other, such as
trifluoromethyl, 1,1-difluoro-1-bromomethyl, and the like.
[0316] The "C1-C6 alkyl group" in the present invention represents,
for example, a linear or branched alkyl group having from 1 to 6
carbon atoms such as methyl, ethyl, n-propyl, propyl, n-butyl,
s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2-pentyl,
n-hexyl, 3-methyl-n-pentyl, and the like.
[0317] The "C1-C6 haloalkyl group" represents, for example, a
linear or branched alkyl group having from 1 to 6 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other, such as trifluoromethyl,
pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl,
2,2-difluoroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl,
2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,
2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2-propyl,
1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl,
1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n-propyl,
4,4,4-trifluoro-n-butyl, 1,1,1,3,3,3-hexafluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl,
2,2,3,3,3-pentafluoro-n-propyl, 3-fluoro-n-propyl,
3-chloro-n-propyl, 3-bromo-n-propyl, 3,3,4,4,4-pentafluoro-2-butyl,
nonafluoro-n-butyl, nonafluoro-2-butyl, 5,5,5-trifluoro-n-pentyl,
4,4,5,5,5-pentafluoro-2-pentyl, 3-chloro-n-pentyl,
4-bromo-2-pentyl, and the like.
[0318] The "C3-C9 cycloalkyl group" represents, for example, a
cycloalkyl group having from 3 to 9 carbon atoms, that has a cyclic
structure, such as cyclopropyl, cyclobutyl, cyclopentyl,
2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl,
2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, and the
like.
[0319] The "C3-C9 halocycloalkyl group" represents, for example, a
cycloalkyl group having 3 to 9 carbon atoms, that is substituted
with one or more halogen atoms which may be the same as or
different from each other and has a cyclic structure, such as,
2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl,
4-chlorocyclohexyl, and the like.
[0320] The "C2-C6 alkenyl group" represents, for example, an
alkenyl group having from 2 to 6 carbon atoms, that has a double
bond in the carbon chain, such as vinyl, allyl, 2-butenyl,
3-butenyl, and the like.
[0321] The "C2-C6 haloalkenyl group" represents, for example, a
linear or branched alkenyl group having from 2 to 6 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other and has a double bond in the
carbon chain, such as 3,3-difluoro-2-propenyl,
3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl,
2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl,
3,4,4-tribromo-3-butenyl, and the like.
[0322] The "C2-C6 alkynyl group" represents, for example, an
alkynyl group having from 2 to 6 carbon atoms, that has a triple
bond in the carbon chain, such as propargyl, 1-butyn-3-yl,
1-butyn-3-methyl-3-yl, and the like.
[0323] The "C2-C6 haloalkynyl group" represents, for example, a
linear or branched alkynyl group having from 2 to 6 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other and has a triple bond in the
carbon chain, such as fluoroethynyl, chloroethynyl, bromoethynyl,
3,3,3-trifluoro-1-propynyl, 3,3,3-trichloro-1-propynyl,
3,3,3-tribromo-1-propynyl, 4,4,4-trifluoro-1-butynyl,
4,4,4-trichloro-1-butynyl, 4,4,4-tribromo-1-butynyl, and the
like.
[0324] The "C1-C6 alkoxy group" represents, for example, a linear,
branched, or cyclic alkoxy group having from 1 to 6 carbon atoms,
such as methoxy, ethoxy, n-propyloxy, i-propyloxy, cyclopropoxy,
n-butoxy, s-butoxy, i-butoxy, t-butoxy, n-pentyloxy, i-pentyloxy,
n-hexyloxy, cyclohexyloxy, and the like.
[0325] The "C1-C6 haloalkoxy group" represents, for example, a
linear, branched, or cyclic alkoxy group having from 1 to 6 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other, such as
trifluoromethoxy, pentafluoroethoxy, 2-chloroethoxy,
2,2,2-trifluoroethoxy, heptafluoro-n-propoxy,
heptafluoro-i-propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy,
3-fluoro-n-propoxy, 1-chlorocyclopropoxy, 2-bromocyclopropoxy,
3,3,4,4,4-pentafluoro-2-butoxy, nonafluoro-n-butoxy,
nonafluoro-2-butoxy, 5,5,5-trifluoro-n-pentyloxy,
4,4,5,5,5-pentafluoro-2-pentyloxy, 3-chloro-n-pentyloxy,
4-bromo-2-pentyloxy, 4-chlorobutyloxy, 2-iodo-n-propyloxy, and the
like.
[0326] The "C1-C6 alkylthio group" represents, for example, a
linear, branched, or cyclic alkylthio group having from 1 to 6
carbon atoms, such as methylthio, ethylthio, n-propylthio,
i-propylthio, cyclopropylthio, n-butylthio, s-butylthio,
i-butylthio, t-butylthio, n-pentylthio, pentylthio, n-hexylthio,
cyclohexylthio, and the like.
[0327] The "C1-C6 haloalkylthio group" represents, for example, a
linear, branched, or cyclic alkylthio group having from 1 to 6
carbon atoms, that is substituted with one or more halogen atoms
which may be the same as or different from each other, such as
trifluoromethylthio, pentafluoroethylthio, 2-chloroethylthio,
2,2,2-trifluoroethylthio, heptafluoro-n-propylthio,
heptafluoro-i-propylthio, 1,1,1,3,3,3-hexafluoro-2-propylthio,
3-fluoro-n-propylthio, 1-chlorocyclopropylthio,
2-bromocyclopropylthio, 3,3,4,4,4-pentafluoro-2-butylthio,
nonafluoro-n-butylthio, nonafluoro-2-butylthio,
5,5,5-trifluoro-n-pentylthio, 4,4,5,5,5-pentafluoro-2-pentylthio,
3-chloro-n-pentylthio, 4-bromo-2-pentylthio, 4-chlorobutylthio,
2-iodo-n-propylthio, and the like.
[0328] The "C1-C6 alkylsulfinyl group" represents, for example, a
linear, branched, or cyclic alkylsulfinyl group having from 1 to 6
carbon atoms, such as methylsulfinyl, ethylsulfinyl,
n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl,
n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butylsulfinyl,
n-pentylsulfinyl, i-pentylsulfinyl, n-hexylsulfinyl,
cyclohexylsulfinyl, and the like.
[0329] The "C1-C6 haloalkylsulfinyl group" represents, for example,
a linear, branched, or cyclic alkylsulfinyl group having from 1 to
6 carbon atoms, that is substituted with one or more halogen atoms
which may be the same as or different from each other, such as
trifluoromethylsulfinyl, pentafluoroethylsulfinyl,
2-chloroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl,
heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl,
1,1,1,3,3,3-hexafluoro-2-propylsulfinyl, 3-fluoro-n-propylsulfinyl,
1-chlorocyclopropylsulfinyl, 2-bromocyclopropylsulfinyl,
3,3,4,4,4-pentafluoro-2-butylsulfinyl, nonafluoro-n-butylsulfinyl,
nonafluoro-2-butylsulfinyl, 5,5,5-trifluoro-n-pentylsulfinyl,
4,4,5,5,5-pentafluoro-2-pentylsulfinyl, 3-chloro-n-pentylsulfinyl,
4-bromo-2-pentylsulfinyl, 4-chlorobutylsulfinyl,
2-iodo-n-propylsulfinyl, and the like.
[0330] The "C1-C6 alkylsulfonyl group" represents, for example, a
linear, branched, or cyclic alkylsulfonyl group having from 1 to 6
carbon atoms, such as methylsulfonyl, ethylsulfonyl,
n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl,
n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butylsulfonyl,
n-pentylsulfonyl, i-pentylsulfonyl, n-hexylsulfonyl,
cyclohexylsulfonyl, and the like.
[0331] The "C1-C6 haloalkylsulfonyl group" represents, for example,
a linear, branched, or cyclic alkylsulfonyl group having from 1 to
6 carbon atoms, that is substituted with one or more halogen atoms
which may be the same as or different from each other, such as
trifluoromethylsulfonyl, pentafluoroethylsulfonyl,
2-chloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,
heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl,
1,1,1,3,3,3-hexafluoro-2-propylsulfonyl, 3-fluoro-n-propylsulfonyl,
1-chlorocyclopropylsulfonyl, 2-bromocyclopropylsulfonyl,
3,3,4,4,4-pentafluoro-2-butylsulfonyl, nonafluoro-n-butylsulfonyl,
nonafluoro-2-butylsulfonyl, 5,5,5-trifluoro-n-pentylsulfonyl,
4,4,5,5,5-pentafluoro-2-pentylsulfonyl, 3-chloro-n-pentylsulfonyl,
4-bromo-2-pentylsulfonyl, 4-chlorobutylsulfonyl,
2-iodo-n-propylsulfonyl, and the like.
[0332] The "C1-C6 alkylsulfonyloxy group" represents, for example,
a linear, branched, or cyclic alkylsulfonyloxy group having from 1
to 6 carbon atoms, such as methanesulfonyloxy, ethanesulfonyloxy,
n-propanesulfonyloxy, i-propanesulfonyloxy,
cyclopropanesulfonyloxy, n-butanesulfonyloxy, s-butanesulfonyloxy,
i-butanesulfonyloxy, t-butanesulfonyloxy, n-pentanesulfonyloxy,
i-pentanesulfonyloxy, n-hexanesulfonyloxy, cyclohexanesulfonyloxy,
and the like.
[0333] The "C1-C6 haloalkylsulfonyloxy group" represents, for
example, a linear, branched, or cyclic alkylsulfonyloxy group
having from 1 to 6 carbon atoms, that is substituted with one or
more halogen atoms which may be the same as or different from each
other, such as trifluoromethanesulfonyloxy,
pentafluoropropanesulfonyloxy, 2-chloropropanesulfonyloxy,
2,2,2-trifluoropropanesulfonyloxy,
heptafluoro-n-propanesulfonyloxy, heptafluoro-i-propanesulfonyloxy,
1,1,1,3,3,3-hexafluoro-2-propanesulfonyloxy,
3-fluoro-n-propanesulfonyloxy, 1-chlorocyclopropanesulfonyloxy,
2-bromocyclopropanesulfonyloxy,
3,3,4,4,4-pentafluoro-2-butanesulfonyloxy,
nonafluoro-n-butanesulfonyloxy, nonafluoro-2-butanesulfonyloxy,
5,5,5-trifluoro-n-pentanesulfonyloxy,
4,4,5,5,5-pentafluoro-2-pentanesulfonyloxy,
3-chloro-n-pentanesulfonyloxy, 4-bromo-2-pentanesulfonyloxy,
4-chlorobutanesulfonyloxy, 2-iodo-n-propanesulfonyloxy, and the
like.
[0334] The "C2-C7 alkylcarbonyl group" represents, for example, a
linear, branched, or cyclic alkylcarbonyl group having from 2 to 7
carbon atoms, such as acetyl, propionyl, propylcarbonyl,
cyclopropylcarbonyl, n-butylcarbonyl, s-butylcarbonyl,
t-butylcarbonyl, n-pentylcarbonyl, 2-pentylcarbonyl,
neopentylcarbonyl, cyclopentylcarbonyl, and the like.
[0335] The "C2-C7 haloalkylcarbonyl group" represents, for example,
a linear, branched, or cyclic alkylcarbonyl group having from 2 to
7 carbon atoms, that is substituted with one or more halogen atoms
which may be the same as or different from each other, such as
trifluoroacetyl, pentafluoropropionyl, 2-chloropropionyl,
2,2,2-trifluoropropionyl, heptafluoro-n-propylcarbonyl,
heptafluoro-i-propylcarbonyl,
1,1,1,3,3,3-hexafluoro-2-propylcarbonyl, 3-fluoro-n-propylcarbonyl,
1-chlorocyclopropylcarbonyl, 2-bromocyclopropylcarbonyl,
3,3,4,4,4-pentafluoro-2-butylcarbonyl, nonafluoro-n-butylcarbonyl,
nonafluoro-2-butylcarbonyl, 5,5,5-trifluoro-n-pentylcarbonyl,
4,4,5,5,5-pentafluoro-2-pentylcarbonyl, 3-chloro-n-pentylcarbonyl,
4-bromo-2-pentylcarbonyl, 4-chlorobutylcarbonyl,
2-iodo-n-propylcarbonyl, and the like.
[0336] The "C2-C7 alkylcarbonyloxy group" represents, for example,
a linear, branched, or cyclic alkylcarbonyloxy group having from 2
to 7 carbon atoms, such as acetyloxy, propionyloxy,
i-propylcarbonyloxy, cyclopropylcarbonyloxy, n-butylcarbonyloxy,
s-butylcarbonyloxy, t-butylcarbonyloxy, n-pentylcarbonyloxy,
2-pentylcarbonyloxy, neopentylcarbonyloxy, cyclopentylcarbonyloxy,
and the like.
[0337] The "C2-C7 haloalkylcarbonyloxy group" represents, for
example, a linear, branched, or cyclic alkylcarbonyloxy group
having from 2 to 7 carbon atoms, that is substituted with one or
more halogen atoms which may be the same as or different from each
other, such as trifluoroacetyloxy, pentafluoropropionyloxy,
2-chloropropionyloxy, 2,2,2-trifluoropropionyloxy,
heptafluoro-n-propylcarbonyloxy, heptafluoro-i-propylcarbonyloxy,
1,1,1,3,3,3-hexafluoro-2-propylcarbonyloxy,
3-fluoro-n-propylcarbonyloxy, 1-chlorocyclopropylcarbonyloxy,
2-bromocyclopropylcarbonyloxy,
3,3,4,4,4-pentafluoro-2-butylcarbonyloxy,
nonafluoro-n-butylcarbonyloxy, nonafluoro-2-butylcarbonyloxy,
5,5,5-trifluoro-n-pentylcarbonyloxy,
4,4,5,5,5-pentafluoro-2-pentylcarbonyloxy,
3-chloro-n-pentylcarbonyloxy, 4-bromo-2-pentylcarbonyloxy,
4-chlorobutylcarbonyloxy, 2-iodo-n-propylcarbonyloxy, and the
like.
[0338] The "C2-C7 alkoxycarbonyl group" represents, for example, a
linear, branched, or cyclic alkoxycarbonyl group having from 2 to 7
carbon atoms, such as methoxycarbonyl, ethoxycarbonyl,
isopropoxycarbonyl, cyclopropoxycarbonyl, n-butoxycarbonyl,
s-butoxycarbonyl, t-butoxycarbonyl, n-pentyloxycarbonyl,
2-pentyloxycarbonyl, neopentyloxycarbonyl, cyclopentyloxycarbonyl,
and the like.
[0339] The "C2-C7 haloalkoxycarbonyl group" represents, for
example, a linear, branched, or cyclic alkoxycarbonyl group having
from 2 to 7 carbon atoms, that is substituted with one or more
halogen atoms which may be the same as or different from each
other, such as trifluoromethoxycarbonyl, pentafluoroethoxycarbonyl,
2-chloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl,
heptafluoro-n-propoxycarbonyl, heptafluoro-i-propoxycarbonyl,
1,1,1,3,3,3-hexafluoro-2-propoxycarbonyl,
3-fluoro-n-propoxycarbonyl, 1-chlorocyclopropoxycarbonyl,
2-bromocyclopropoxycarbonyl,
3,3,4,4,4-pentafluoro-2-butoxycarbonyl,
nonafluoro-n-butoxycarbonyl, nonafluoro-2-butoxycarbonyl,
5,5,5-trifluoro-n-pentyloxycarbonyl,
4,4,5,5,5-pentafluoro-2-pentyloxycarbonyl,
3-chloro-n-pentyloxycarbonyl, 4-bromo-2-pentyloxycarbonyl,
4-chlorobutyloxycarbonyl, 2-iodo-n-propyloxycarbonyl, and the
like.
[0340] The "C2-C7 alkylcarbonylamino group" represents, for
example, a linear, branched, or cyclic alkylcarbonylamino group
having from 2 to 7 carbon atoms, such as acetylamino,
propionylamino, n-propylcarbonylamino, i-propylcarbonylamino,
cyclopropylcarbonylamino, n-butylcarbonylamino,
s-butylcarbonylamino, i-butylcarbonylamino, t-butylcarbonylamino,
n-pentylcarbonylamino, i-pentylcarbonylamino, n-hexylcarbonylamino,
cyclohexylcarbonylamino, and the like.
[0341] The "C2-C7 haloalkylcarbonylamino group" represents, for
example, a linear, branched, or cyclic alkylcarbonylamino group
having from 2 to 7 carbon atoms, that is substituted with one or
more halogen atoms which may be the same as or different from each
other, such as trifluoroacetylamino, pentafluoropropionylamino,
2-chloropropionylamino, 2,2,2-trifluoropropionylamino,
heptafluoro-n-propylcarbonylamino,
heptafluoro-i-propylcarbonylamino,
1,1,1,3,3,3-hexafluoro-2-propylcarbonylamino,
3-fluoro-n-propylcarbonylamino, 1-chlorocyclopropylcarbonylamino,
2-bromocyclopropylcarbonylamino,
3,3,4,4,4-pentafluoro-2-butylcarbonylamino,
nonafluoro-n-butylcarbonylamino, nonafluoro-2-butylcarbonylamino,
5,5,5-trifluoro-n-pentylcarbonylamino,
4,4,5,5,5-pentafluoro-2-pentylcarbonylamino,
3-chloro-n-pentylcarbonylamino, 4-bromo-2-pentylcarbonylamino,
4-chlorobutylcarbonylamino, 2-iodo-n-propylcarbonylamino, and the
like.
[0342] The "C2-C7 alkoxycarbonylamino group" represents, for
example, a linear, branched, or cyclic alkoxycarbonylamino group
having from 2 to 7 carbon atoms, such as methoxycarbonylamino,
ethoxycarbonylamino, n-propyloxycarbonylamino,
propyloxycarbonylamino, cyclopropoxycarbonylamino,
n-butoxycarbonylamino, s-butoxycarbonylamino,
i-butoxycarbonylamino, t-butoxycarbonylamino,
n-pentyloxycarbonylamino, i-pentyloxycarbonylamino,
n-hexyloxycarbonylamino, cyclohexyloxycarbonylamino, and the
like.
[0343] The "C2-C7 haloalkoxycarbonylamino group" represents, for
example, a linear, branched, or cyclic alkoxycarbonylamino group
having from 2 to 7 carbon atoms, that is substituted with one or
more halogen atoms which may be the same as or different from each
other, such as trifluoromethoxycarbonylamino,
pentafluoroethoxycarbonylamino, 2-chloroethoxycarbonylamino,
2,2,2-trifluoroethoxycarbonylamino,
heptafluoro-n-propoxycarbonylamino,
heptafluoro-i-propoxycarbonylamino,
1,1,1,3,3,3-hexafluoro-2-propoxycarbonylamino,
3-fluoro-n-propoxycarbonylamino, 1-chlorocyclopropoxycarbonylamino,
2-bromocyclopropoxycarbonylamino,
3,3,4,4,4-pentafluoro-2-butoxycarbonylamino,
nonafluoro-n-butoxycarbonylamino, nonafluoro-2-butoxycarbonylamino,
5,5,5-trifluoro-n-pentyloxycarbonylamino,
4,4,5,5,5-pentafluoro-2-pentyloxycarbonylamino,
3-chloro-n-pentyloxycarbonylamino,
4-bromo-2-pentyloxycarbonylamino, 4-chlorobutyloxycarbonylamino,
2-iodo-n-propyloxycarbonylamino, and the like.
[0344] The "C2-C7 alkoxycarbonyloxy group" represents, for example,
a linear, branched, or cyclic alkoxycarbonyloxy group having from 2
to 7 carbon atoms, such as methoxycarbonyloxy, ethoxycarbonyloxy,
n-propyloxycarbonyloxy, i-propyloxycarbonyloxy,
cyclopropoxycarbonyloxy, n-butoxycarbonyloxy, s-butoxycarbonyloxy,
i-butoxycarbonyloxy, t-butoxycarbonyloxy, n-pentyloxycarbonyloxy,
i-pentyloxycarbonyloxy, n-hexyloxycarbonyloxy,
cyclohexyloxycarbonyloxy, and the like.
[0345] The "C2-C7 haloalkoxycarbonyloxy group" represents, for
example, a linear, branched, or cyclic alkoxycarbonyloxy group
having from 2 to 7 carbon atoms, that is substituted with one or
more halogen atoms which may be the same as or different from each
other, such as trifluoromethoxycarbonyloxy,
pentafluoroethoxycarbonyloxy, 2-chloroethoxycarbonyloxy,
2,2,2-trifluoroethoxycarbonyloxy, heptafluoro-n-propoxycarbonyloxy,
heptafluoro-i-propoxycarbonyloxy,
1,1,1,3,3,3-hexafluoro-2-propoxycarbonyloxy,
3-fluoro-n-propoxycarbonyloxy, 1-chlorocyclopropoxycarbonyloxy,
2-bromocyclopropoxycarbonyloxy,
3,3,4,4,4-pentafluoro-2-butoxycarbonyloxy,
nonafluoro-n-butoxycarbonyloxy, nonafluoro-2-butoxycarbonyloxy,
5,5,5-trifluoro-n-pentyloxycarbonyloxy,
4,4,5,5,5-pentafluoro-2-pentyloxycarbonyloxy,
3-chloro-n-pentyloxycarbonyloxy, 4-bromo-2-pentyloxycarbonyloxy,
4-chlorobutyloxycarbonyloxy, 2-iodo-n-propyloxycarbonyloxy, and the
like.
[0346] The "C1-C6 alkylamino group" represents, for example, a
linear, branched, or cyclic alkylamino group having from 1 to 6
carbon atoms, such as methylamino, dimethylamino, ethylamino,
diethylamino, n-propylamino, i-propylamino, cyclopropylamino,
n-butylamino, s-butylamino, i-butylamino, t-butylamino,
n-pentylamino, i-pentylamino, n-hexylamino, cyclohexylamino, and
the like.
[0347] The "C1-C6 haloalkylamino group" represents, for example, a
linear, branched, or cyclic alkylamino group having from 1 to 6
carbon atoms substituted with one or more halogen atoms which may
be the same as or different from each other, such as
trifluoromethylamino, ditrifluoromethylamino,
pentafluoroethylamino, dipentafluoroethylamino, 2-chloroethylamino,
2,2,2-trifluoroethylamino, heptafluoro-n-propylamino,
heptafluoro-i-propylamino, 1,1,1,3,3,3-hexafluoro-2-propylamino,
3-fluoro-n-propylamino, 1-chlorocyclopropylamino,
2-bromocyclopropylamino, 3,3,4,4,4-pentafluoro-2-butylamino,
nonafluoro-n-butylamino, nonafluoro-2-butylamino,
5,5,5-trifluoro-n-pentylamino, 4,4,5,5,5-pentafluoro-2-pentylamino,
3-chloro-n-pentylamino, 4-bromo-2-pentylamino, 4-chlorobutylamino,
2-iodo-n-propylamino, and the like.
[0348] The "C2-C6 alkenyloxy group" represents, for example, an
alkenyloxy group having from 2 to 6 carbon atoms, that has a double
bond in the carbon chain, such as vinyloxy, allyloxy, 2-butenyloxy,
3-butenyloxy, and the like.
[0349] The "C2-C6 haloalkenyloxy group" represents, for example, a
linear or branched alkenyloxy group having from 2 to 6 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other and has a double bond
in the carbon chain, such as 3,3-difluoro-2-propenyloxy,
3,3-dichloro-2-propenyloxy, 3,3-dibromo-2-propenyloxy,
2,3-dibromo-2-propenyloxy, 4,4-difluoro-3-butenyloxy,
3,4,4-tribromo-3-butenyloxy, and the like.
[0350] The "C2-C6 alkynyloxy group" represents, for example, an
alkynyloxy group having from 2 to 6 carbon atoms, that has a triple
bond in the carbon chain, such as propargyloxy, 1-butyn-3-yloxy,
1-butyn-3-methyl-3-yloxy, and the like.
[0351] The "C2-C6 haloalkynyloxy group" represents, for example, a
linear or branched alkynyloxy group having from 2 to 6 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other and has a triple bond
in the carbon chain, such as fluoroethynyloxy, chloroethynyloxy,
bromoethynyloxy, 3,3,3-trifluoro-1-propynyloxy,
3,3,3-trichloro-1-propynyloxy, 3,3,3-tribromo-1-propynyloxy,
4,4,4-trifluoro-1-butynyloxy, 4,4,4-trichloro-1-butynyloxy,
4,4,4-tribromo-1-butynyloxy, and the like.
[0352] The "C3-C9 cycloalkoxy group" represents, for example, a
cycloalkyloxy group having from 3 to 9 carbon atoms, that has a
cyclic structure, such as cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy, 2-methylcyclopentyloxy, 3-methylcyclopentyloxy,
cyclohexyloxy, 2-methylcyclohexyloxy, 3-methylcyclohexyloxy,
4-methylcyclohexyloxy, and the like.
[0353] The "C3-C9 halocycloalkoxy group" represents, for example, a
cycloalkyloxy group having from 3 to 9 carbon atoms, that is
substituted with one or more halogen atoms which may be the same as
or different from each other and has a cyclic structure, such as
2,2,3,3-tetrafluorocyclobutyloxy, 2-chlorocyclohexyloxy,
4-chlorocyclohexyloxy, and the like.
[0354] The "C3-C7 alkenylcarbonyl group" represents, for example,
an alkenylcarbonyl group having from 3 to 7 carbon atoms, that has
a double bond in the carbon chain, such as vinylcarbonyl,
allylcarbonyl, 2-butenylcarbonyl, 3-butenylcarbonyl, and the
like.
[0355] The "C3-C7 haloalkenylcarbonyl group" represents an
alkenylcarbonyl group having from 3 to 7 carbon atoms, that is
substituted with one or more halogen atoms which may be the same as
or different from each other and has a double bond in the carbon
chain, such as 3,3-difluoro-2-propenylcarbonyl,
3,3-dichloro-2-propenylcarbonyl, 3,3-dibromo-2-propenylcarbonyl,
2,3-dibromo-2-propenylcarbonyl, 4,4-difluoro-3-butenylcarbonyl,
3,4,4-tribromo-3-butenylcarbonyl, and the like.
[0356] The "C3-C7 alkynylcarbonyl group" represents an
alkynylcarbonyl group having from 3 to 7 carbon atoms and has a
triple bond in the carbon chain, such as propargylcarbonyl,
1-butyn-3-ylcarbonyl, 1-butyn-3-methyl-3-ylcarbonyl, and the
like.
[0357] The "C3-C7 haloalkynylcarbonyl group" represents, for
example, a linear or branched alkynylcarbonyl group having from 3
to 7 carbon atoms, that is substituted with one or more halogen
atoms which may be the same as or different from each other and has
a triple bond in the carbon chain, such as fluoroethynylcarbonyl,
chloroethynylcarbonyl, bromoethynylcarbonyl,
3,3,3-trifluoro-1-propynylcarbonyl,
3,3,3-trichloro-1-propynylcarbonyl,
3,3,3-tribromo-1-propynylcarbonyl,
4,4,4-trifluoro-1-butynylcarbonyl,
4,4,4-trichloro-1-butynylcarbonyl,
4,4,4-tribromo-1-butynylcarbonyl, and the like.
[0358] The "C4-C10 cycloalkylcarbonyl group" represents, for
example, a cycloalkylcarbonyl group having from 4 to 10 carbon
atoms, that has a cyclic structure, such as cyclopropylcarbonyl,
cyclobutylcarbonyl, cyclopentylcarbonyl,
2-methylcyclopentylcarbonyl, 3-methylcyclopentylcarbonyl,
cyclohexylcarbonyl, 2-methylcyclohexylcarbonyl,
3-methylcyclohexylcarbonyl, 4-methylcyclohexylcarbonyl, and the
like.
[0359] The "C4-C10 halocycloalkylcarbonyl group" represents, for
example, a cycloalkylcarbonyl group having from 4 to 10 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other and has a cyclic
structure, such as 2,2,3,3-tetrafluorocyclobutylcarbonyl,
2-chlorocyclohexylcarbonyl, 4-chlorocyclohexylcarbonyl, and the
like.
[0360] The "C3-C7 alkenyloxycarbonyl group" represents an
alkenyloxycarbonyl group having 3 to 7 carbon atoms, that has a
double bond in the carbon chain, such as vinyloxycarbonyl,
allyloxycarbonyl, 2-butenyloxycarbonyl, 3-butenyloxycarbonyl, and
the like.
[0361] The "C3-C7 haloalkenyloxycarbonyl group" represents, for
example, a linear or branched alkenyloxycarbonyl group having from
3 to 7 carbon atoms, that is substituted with one or more halogen
atoms which may be the same as or different from each other and has
a double bond in the carbon chain, such as
3,3-difluoro-2-propenyloxycarbonyl,
3,3-dichloro-2-propenyloxycarbonyl,
3,3-dibromo-2-propenyloxycarbonyl,
2,3-dibromo-2-propenyloxycarbonyl,
4,4-difluoro-3-butenyloxycarbonyl,
3,4,4-tribromo-3-butenyloxycarbonyl, and the like.
[0362] The "C3-C7 alkynyloxycarbonyl group" represents, for
example, an alkynyloxycarbonyl group having from 3 to 7 carbon
atoms, that has a triple bond in the carbon chain, such as
propargyloxycarbonyl, 1-butyn-3-yloxycarbonyl,
1-butyn-3-methyl-3-yloxycarbonyl, and the like.
[0363] The "C3-C7 haloalkynyloxycarbonyl group" represents, for
example, a linear or branched alkynyloxycarbonyl group having from
3 to 7 carbon atoms, that is substituted with one or more halogen
atoms which may be the same as or different from each other and has
a triple bond in the carbon chain, such as
fluoroethynyloxycarbonyl, chloroethynyloxycarbonyl,
bromoethynyloxycarbonyl, 3,3,3-trifluoro-1-propynyloxycarbonyl,
3,3,3-trichloro-1-propynyloxycarbonyl,
3,3,3-tribromo-1-propynyloxycarbonyl,
4,4,4-trifluoro-1-butynyloxycarbonyl,
4,4,4-trichloro-1-butynyloxycarbonyl,
4,4,4-tribromo-1-butynyloxycarbonyl, and the like.
[0364] The "C4-C10 cycloalkyloxycarbonyl group" represents, for
example, a cycloalkyloxycarbonyl group having from 4 to 10 carbon
atoms, that has a cyclic structure, such as cyclopropyloxycarbonyl,
cyclobutyloxycarbonyl, cyclopentyloxycarbonyl,
2-methylcyclopentyloxycarbonyl, 3-methylcyclopentyloxycarbonyl,
cyclohexyloxycarbonyl, 2-methylcyclohexyloxycarbonyl,
3-methylcyclohexyloxycarbonyl, 4-methylcyclohexyloxycarbonyl, and
the like.
[0365] The "C4-C10 halocycloalkyloxycarbonyl group" represents, for
example, a cycloalkyloxycarbonyl group having from 4 to 10 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other and has a cyclic
structure, such as 2,2,3,3-tetrafluorocyclobutyloxycarbonyl,
2-chlorocyclohexyloxycarbonyl, 4-chlorocyclohexyloxycarbonyl, and
the like.
[0366] The "C2-C6 alkenylamino group" represents, for example, an
alkenylamino group having 2 to 6 carbon atoms, that has a double
bond in the carbon chain, such as vinylamino, allylamino,
2-butenylamino, 3-butenylamino, and the like.
[0367] The "C2-C6 haloalkenylamino group" represents a linear or
branched alkenylamino group having from 2 to 6 carbon atoms, that
is substituted with one or more halogen atoms which may be the same
as or different from each other and has a double bond in the carbon
chain, such as 3,3-difluoro-2-propenylamino,
3,3-dichloro-2-propenylamino, 3,3-dibromo-2-propenylamino,
2,3-dibromo-2-propenylamino, 4,4-difluoro-3-butenylamino,
3,4,4-tribromo-3-butenylamino, and the like.
[0368] The "C2-C6 alkynylamino group" represents, for example, an
alkynylamino group having from 2 to 6 carbon atoms, that has a
triple bond in the carbon chain, such as propargylamino,
1-butyn-3-ylamino, 1-butyn-3-methyl-3-ylamino, and the like.
[0369] The "C2-C6 haloalkynylamino group" represents, for example,
a linear or branched alkynylamino group having from 2 to 6 carbon
atoms, that is substituted with one or more halogen atoms which may
be the same as or different from each other and has a triple bond
in the carbon chain, such as fluoroethynylamino,
chloroethynylamino, bromoethynylamino,
3,3,3-trifluoro-1-propynylamino, 3,3,3-trichloro-1-propynylamino,
3,3,3-tribromo-1-propynylamino, 4,4,4-trifluoro-1-butynylamino,
4,4,4-trichloro-1-butynylamino, 4,4,4-tribromo-1-butynylamino, and
the like.
[0370] The "C3-C9 cycloalkylamino group" represents, for example, a
cycloalkyl group amino having from 3 to 9 carbon atoms, that has a
cyclic structure, such as cyclopropylamino, cyclobutylamino,
cyclopentylamino, 2-methylcyclopentylamino,
3-methylcyclopentylamino, cyclohexylamino, 2-methylcyclohexylamino,
3-methylcyclohexylamino, 4-methylcyclohexylamino, and the like.
[0371] The "C3-C9 halocycloalkylamino group" represents, for
example, a cycloalkylamino group having from 3 to 9 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other and has a cyclic structure,
such as 2,2,3,3-tetrafluorocyclobutylamino,
2-chlorocyclohexylamino, 4-chlorocyclohexylamino, and the like.
[0372] The "C2-C7 alkylaminocarbonyl group" represents, for
example, a linear or branched alkylaminocarbonyl group having from
2 to 7 carbon atoms, such as methylaminocarbonyl,
ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl,
n-butylaminocarbonyl, s-butylaminocarbonyl, t-butylaminocarbonyl,
n-pentylaminocarbonyl, 2-pentylaminocarbonyl,
neopentylaminocarbonyl, 4-methyl-2-pentylaminocarbonyl,
n-hexylaminocarbonyl, 3-methyl-n-pentylaminocarbonyl, and the
like.
[0373] The "C2-C7 haloalkylaminocarbonyl group" represents, for
example, a linear or branched alkylaminocarbonyl group having from
2 to 7 carbon atoms, that is substituted with one or more halogen
atoms which may be the same as or different from each other, such
as trifluoromethylaminocarbonyl, pentafluoroethylaminocarbonyl,
heptafluoro-n-propylaminocarbonyl,
heptafluoro-i-propylaminocarbonyl, 2,2-difluoroethylaminocarbonyl,
2,2-dichloroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl,
2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl,
2-bromoethylaminocarbonyl, 2-iodoethylaminocarbonyl,
2,2,2-trichloroethylaminocarbonyl,
2,2,2-tribromoethylaminocarbonyl,
1,3-difluoro-2-propylaminocarbonyl,
1,3-dichloro-2-propylaminocarbonyl,
1-chloro-3-fluoro-2-propylaminocarbonyl,
1,1,1-trifluoro-2-propylaminocarbonyl,
2,3,3,3-trifluoro-n-propylaminocarbonyl,
4,4,4-trifluoro-n-butylaminocarbonyl,
1,1,1,3,3,3-hexafluoro-2-propylaminocarbonyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propylaminocarbonyl,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propylaminocarbonyl,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propylaminocarbonyl,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propylaminocarbonyl,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propylaminocarbonyl,
2,2,3,3,3-pentafluoro-n-propylaminocarbonyl,
3-fluoro-n-propylaminocarbonyl, 3-chloro-n-propylaminocarbonyl,
3-bromo-n-propylaminocarbonyl,
3,3,4,4,4-pentafluoro-2-butylaminocarbonyl,
nonafluoro-n-butylaminocarbonyl, nonafluoro-2-butylaminocarbonyl,
5,5,5-trifluoro-n-pentylaminocarbonyl,
4,4,5,5,5-pentafluoro-2-pentylaminocarbonyl,
3-chloro-n-pentylaminocarbonyl, 4-bromo-2-pentylaminocarbonyl, and
the like.
[0374] The "C3-C7 alkenylaminocarbonyl group" represents, for
example, an alkenylaminocarbonyl group having from 3 to 7 carbon
atoms, that has a double bond in the carbon chain, such as
vinylaminocarbonyl, allylaminocarbonyl, 2-butenylaminocarbonyl,
3-butenylaminocarbonyl, and the like.
[0375] The "C3-C7 haloalkenylaminocarbonyl group" represents, for
example, a linear or branched alkenylaminocarbonyl group having
from 3 to 7 carbon atoms, that is substituted with one or more
halogen atoms which may be the same as or different from each other
and has a double bond in the carbon chain, such as
3,3-difluoro-2-propenylaminocarbonyl,
3,3-dichloro-2-propenylaminocarbonyl,
3,3-dibromo-2-propenylaminocarbonyl,
2,3-dibromo-2-propenylaminocarbonyl,
4,4-difluoro-3-butenylaminocarbonyl,
3,4,4-tribromo-3-butenylaminocarbonyl, and the like.
[0376] The "C3-C7 alkynylaminocarbonyl group" represents, for
example, an alkynylaminocarbonyl group having from 3 to 7 carbon
atoms, that has a triple bond in the carbon chain, such as
propargylaminocarbonyl, 1-butyn-3-ylaminocarbonyl,
1-butyn-3-methyl-3-ylaminocarbonyl, and the like.
[0377] The "C3-C7 haloalkynylaminocarbonyl group" represents, for
example, a linear or branched alkynylaminocarbonyl group having
from 3 to 7 carbon atoms, that is substituted with one or more
halogen atoms which may be the same as or different from each other
and has a triple bond in the carbon chain, such as
fluoroethynylaminocarbonyl, chloroethynylaminocarbonyl,
bromoethynylaminocarbonyl, 3,3,3-trifluoro-1-propynylaminocarbonyl,
3,3,3-trichloro-1-propynylaminocarbonyl,
3,3,3-tribromo-1-propynylaminocarbonyl,
4,4,4-trifluoro-1-butynylaminocarbonyl,
4,4,4-trichloro-1-butynylaminocarbonyl,
4,4,4-tribromo-1-butynylaminocarbonyl, and the like.
[0378] The "C4-C10 cycloalkylaminocarbonyl group" represents, for
example, a cycloalkylaminocarbonyl group having from 4 to 10 carbon
atoms, that has a cyclic structure, such as
cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
cyclopentylaminocarbonyl, 2-methylcyclopentylaminocarbonyl,
3-methylcyclopentylaminocarbonyl, cyclohexylaminocarbonyl,
2-methylcyclohexylaminocarbonyl, 3-methylcyclohexylaminocarbonyl,
4-methylcyclohexylaminocarbonyl, and the like.
[0379] The "C4-C10 halocycloalkylaminocarbonyl group" represents,
for example, a cycloalkylaminocarbonyl group having from 4 to 10
carbon atoms that is substituted with one or more halogen atoms
which may be the same as or different from each other and has a
cyclic structure, such as 2,3,3-tetrafluorocyclobutylaminocarbonyl,
2-chlorocyclohexylaminocarbonyl, 4-chlorocyclohexylaminocarbonyl,
and the like.
[0380] The "aryl group" represents, for example, a monocyclic and
polycyclic aromatic hydrocarbon, such as phenyl group, naphtyl
group, and the like.
[0381] The "arylcarbonyloxy group" represents, for example, a
arylcarbonyloxy group, such as phenylcarbonyloxy group,
naphthylcarbonyloxy group, and the like.
[0382] The "arylcarbonylamino group" represents, for example, a
arylcarbonylamino group, such as phenylcarbonylamino group,
naphthylcarbonylamino group, and the like.
[0383] The "C1-C6 alkyl group which may have a substituent" in
R.sub.1 and R.sub.2 represents an unsubstituted linear, branched,
or cyclic alkyl group having 1 to 6 carbon atoms, or a linear,
branched, or cyclic alkyl group having from 1 to 6 carbon atoms,
which is substituted only with at least one of a nitro group, a
phenyl group which may have a substituent, and an unsaturated
heterocyclic group which may have a substituent. Further, when
there are two or more substituents, these substituents may be the
same as or different from each other.
[0384] The "C1-C6 haloalkyl group which may have a substituent" in
R.sub.1 and R.sub.2 represents a linear, branched, or cyclic alkyl
group having from 1 to 6 carbon atoms, which is substituted with
one or more halogen atoms, or a linear, branched, or cyclic alkyl
group having 1 to 6 carbon atoms, which is substituted with at
least one of a nitro group, a phenyl group which may have a
substituent, and an unsaturated heterocyclic group which may have a
substituent, in addition to one or more halogen atoms.
[0385] The "C2-C6 alkenyl group which may have a substituent" in
R.sub.1 and R.sub.2 represents an unsubstituted linear, branched,
or cyclic alkenyl group having from 2 to 6 carbon atoms, or a
linear, branched, or cyclic alkenyl group having 2 to 6 carbon
atoms, which is substituted with at least one of a nitro group, a
phenyl group which may have a substituent, and an unsaturated
heterocyclic group which may have a substituent. Further, when
there are two or more substituents, these substituents may be the
same as or different from each other.
[0386] The "C2-C6 haloalkenyl group which may have a substituent"
in R.sub.1 and R.sub.2 represents a linear, branched, or cyclic
alkenyl group having from 2 to 6 carbon atoms, which is substituted
only with one or more halogen atoms, or a linear, branched, or
cyclic alkenyl group having 2 to 6 carbon atoms, which is
substituted with at least one of a nitro group, a phenyl group
which may have a substituent, and an unsaturated heterocyclic group
which may have a substituent, in addition to one or more halogen
atoms.
[0387] The "C2-C6 alkynyl group which may have a substituent" in
R.sub.1 and R.sub.2 represents an unsubstituted linear, branched,
or cyclic alkynyl group having from 2 to 6 carbon atoms, or a
linear, branched, or cyclic alkynyl group having 2 to 6 carbon
atoms, which is substituted with at least one of a nitro group, a
phenyl group which may have a substituent, and an unsaturated
heterocyclic group which may have a substituent. Further, when
there are two or more substituents, these substituents may be the
same as or different from each other.
[0388] The "C2-C6 haloalkynyl group which may have a substituent"
in R.sub.1 and R.sub.2 represents a linear, branched, or cyclic
alkynyl group having from 2 to 6 carbon atoms, which is substituted
only with one or more halogen atoms, or a linear, branched, or
cyclic alkynyl group having 2 to 6 carbon atoms, which is
substituted with at least one of a nitro group, a phenyl group
which may have a substituent, and an unsaturated heterocyclic group
which may have a substituent, in addition to one or more halogen
atoms.
[0389] Further, each of the substituents in the present invention
may further have a substituent, and examples of the substituent
include the following:
[0390] one or more substituents selected from a group consisting of
a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C3-C9 cycloalkyl group, a C3-C9 halocycloalkyl group, a C2-C6
alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a
C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C2-C7
alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, a C2-C7
alkylcarbonyloxy group, a C2-C7 haloalkylcarbonyloxy group, a C1-C6
alkylsulfonyloxy group, a C1-C6 haloalkylsulfonyloxy group, a C2-C7
alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C2-C7
alkylcarbonylamino group, a C2-C7 haloalkylcarbonylamino group, a
C2-C7 alkoxycarbonylamino group, a C2-C7 haloalkoxycarbonylamino
group, a C2-C7 alkylaminocarbonyl group, a C2-C7
haloalkylaminocarbonyl group, a C1-C6 alkylamino group, a C1-C6
haloalkylamino group, a C2-C6 alkenylamino group, a C2-C6
haloalkenylamino group, a C2-C6 alkynylamino group, a C2-C6
haloalkynylamino group, a C3-C9 cycloalkylamino group, a C3-C9
halocycloalkylamino group, a C3-C7 alkenylaminocarbonyl group, a
C3-C7 haloalkenylaminocarbonyl group, a C3-C7 alkynylaminocarbonyl
group, a C3-C7 haloalkynylaminocarbonyl group, a C4-C10
cycloalkylaminocarbonyl group, a C4-C10 halocycloalkylaminocarbonyl
group, an amino group, a carbamoyl group, a sulfamoyl group, a
cyano group, a nitro group, a hydroxyl group, a carboxylic group, a
pentafluorosulfanyl group, a phenyl group which may have a
substituent, a heterocyclic group which may have a substituent, a
benzyl group which may have a substituent, a phenylcarbonyl group
which may have a substituent, and a phenylamino group which may
have a substituent, and when there are two or more substituents,
each substituent may be the same as or different from each
other.
[0391] The compounds represented by Formula (1), Formula (7),
Formula (8), and the like of the present invention may include one
or plural chiral carbon atoms or chiral centers in their structural
Formulae, and thus two or more optical isomers may exist. However,
the present invention includes each of the optical isomers and a
mixture thereof at any proportions. Further, the compounds
represented by Formula (1), Formula (7), Formula (8), and the like
of the present invention may include two or more kinds of
geometrical isomers derived from carbon-carbon double bonds in the
structural Formulae. However, the present invention includes each
of the geometrical isomers and a mixture thereof at any
proportions.
[0392] The combinations of the substituents or atoms preferred as
the substituents or the like for the amide derivative represented
by Formula (1) of the present invention are as follows.
[0393] T is preferably --C(=G.sub.1)-Q.sub.1, G.sub.1 is preferably
an oxygen atom, Q.sub.1 is preferably a phenyl group which may have
a substituent, or a pyridyl group which may have a substituent, and
Q.sub.1 is more preferably a phenyl group or a pyridyl group which
has one or more substituents selected from a group consisting of a
halogen atom, a C1 haloalkyl group, a nitro group, and a cyano
group, and when there are two or more substituents, each
substituent may be the same as or different from each other.
[0394] G.sub.3 is preferably an oxygen atom.
[0395] R.sub.1 is preferably a hydrogen atom or a C1-C3 alkyl
group.
[0396] R.sub.2 is preferably a hydrogen atom.
[0397] A is preferably a carbon atom, and K is preferably a
non-metal atom group which is combined with A and two carbon atoms
to which A bonds to faun a benzene ring.
[0398] X is preferably a hydrogen atom, a halogen atom, or a cyano
group, and more preferably a hydrogen atom, a fluorine atom, or a
cyano group.
[0399] When X is a substituent other than a hydrogen atom, n is
preferably 0, 1, or 2.
[0400] Y.sub.1 is preferably a halogen atom or a C1-C3 haloalkyl
group.
[0401] Y.sub.5 is preferably a C1-C3 haloalkyl group.
[0402] Y.sub.2 and Y.sub.4 are preferably hydrogen atoms, halogen
atoms, or C1-C4 alkyl groups, and more preferably hydrogen
atoms.
[0403] Y.sub.3 is preferably a C2-C5 haloalkyl group, and more
preferably a C2-C4 perfluoroalkyl group.
[0404] Furthermore, the combinations of the substituent or atom
preferred as the substituent and the like for the amide derivative
represented by Formula (8) are as follows.
[0405] Q.sub.1 is preferably a phenyl group or a pyridyl group
which has one or more substituents selected from a group consisting
of a halogen atom, a C1 haloalkyl group, a nitro group, and a cyano
group, and when there are two or more substituents, each
substituent may be the same as or different from each other.
[0406] R.sub.1 is preferably a hydrogen atom or a C1-C3 alkyl
group.
[0407] R.sub.2 is preferably a hydrogen atom.
[0408] X.sub.1 and X.sub.2 are preferably hydrogen atoms or
fluorine atoms, and X.sub.3 and X.sub.4 are preferably hydrogen
atoms.
[0409] Y.sub.1 and Y.sub.5 are preferably halogen atoms or C1-C3
haloalkyl groups. Y.sub.2 and Y.sub.4 are preferably hydrogen
atoms. Y.sub.3 is preferably a C3-C4 perfluoroalkyl group.
[0410] The representative methods for producing the compound of the
present invention are shown below, and the method for producing the
amide derivative of the present invention is not limited to the
preparation methods below.
[0411] In Formula shown in the following preparation method, A, K,
X, n, R.sub.1, R.sub.2, T, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3,
Y.sub.4, and Y.sub.5 represent the same definitions as A, K, X, n,
R.sub.1, R.sub.2, T, G.sub.3, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4,
and Y.sub.5, respectively, in Formula (1). LG represents a
functional group having a leaving ability, such as a halogen atom,
a hydroxy group, or the like, Hal represents a chlorine atom or a
bromine atom, and Xa, Xb, and Xc represent chlorine atoms, bromine
atoms, or iodine atoms.
[0412] <Preparation Method 1>
##STR00114## Formula (21)+Formula (22).fwdarw.Formula (23)
Formula (21)+Formula (22).fwdarw.Formula (28) 1-(i)
[0413] A nitro aromatic carboxamide derivative represented by
Formula (23) or Formula (28) can be prepared by reacting a nitro
aromatic carboxylic acid derivative having a leaving group
represented by Formula (21) with an aromatic amine derivative
represented by Formula (22) in a suitable solvent or without a
solvent. In the present step, a suitable base can be used.
[0414] The solvent may be any of those which do not inhibit the
present reaction significantly. Examples thereof may include water
and aromatic hydrocarbons such as benzene, toluene, xylene, and the
like, halogenated hydrocarbons such as dichloromethane, chloroform,
carbon tetrachloride, and the like, chained or cyclic ethers such
as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane,
and the like, esters such as ethyl acetate, butyl acetate, and the
like, alcohols such as methanol, ethanol, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, and the
like, amides such as dimethyl formamide, dimethylacetamide, and the
like, nitriles such as acetonitrile and the like, and inert
solvents such as 1,3-dimethyl-2-imidazolidinone and the like. These
solvents may be used alone or as a mixture of two or more kinds
thereof.
[0415] Furthermore, examples of the base may include organic bases
such as triethylamine, tri-n-butyl amine, pyridine, 4-dimethylamino
pyridine, and the like, alkali metal hydroxides such as sodium
hydroxide, potassium hydroxide, and the like, carbonates such as
sodium hydrogen carbonate, potassium carbonate, and the like,
phosphates such as dipotassium monohydrogen phosphate, trisodium
phosphate, and the like, alkali metal hydride salts such as sodium
hydride and the like, alkali metal alkoxides such as sodium
methoxide, sodium ethoxide, and the like, and lithium amides such
as lithium diisopropyl amide, and the like.
[0416] These bases may be appropriately used in an amount in the
range from 0.01-fold molar equivalent to 5-fold molar equivalents
with respect to the compound represented by Formula (21).
[0417] The reaction temperature may be appropriately selected from
-20.degree. to the reflux temperature of the solvent used. Further,
the reaction time may be appropriately selected within the range
from several minutes to 96 hours.
[0418] Among the compounds represented by Formula (21), the
aromatic carbonyl halide derivative can be prepared easily by a
general method using a halogenating agent from an aromatic
carboxylic acid. Examples of the halogenating agent include thionyl
chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride,
phosphorus trichloride, and the like.
[0419] Meanwhile, it is possible to prepare the compound
represented by Formula (23) or Formula (28) from the nitro aromatic
carboxylic acid derivative and the compound represented by Formula
(22) without using a halogenating agent. Examples of the method may
include a method described in, for example, Chem. Ber. p. 788
(1970), in which a condensing agent such as
N,N'-dicyclohexylcarbodiimide and the like is appropriately used,
suitably with the use of an additive such as 1-hydroxybenzotriazole
and the like. Other condensing agents that can be used in this case
may include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide,
1,1'-carbonylbis-1H-imidazole, and the like.
[0420] Furthermore, examples of other methods for producing the
compound represented by Formula (23) or Formula (28) may include a
mixed anhydride method using chloroformic acid esters, and examples
thereof include a method described in J. Am. Chem. Soc., p. 5012
(1967), whereby the compound represented by Formula (23) or Formula
(28) can be prepared. Examples of the chloroformic acid esters used
in this case may include isobutyl chloroformate, isopropyl
chloroformate and the like. In addition to chloroformic acid
esters, diethylacetyl chloride, trimethylacetyl chloride and the
like may also be included.
[0421] Both the method using a condensing agent and the mixed
anhydride method are not limited by the solvent, the reaction
temperature, and the reaction time according to the literature
above. An inert solvent may be used which does not inhibit the
progress of the appropriate reaction significantly, and the
reaction temperature and the reaction time may also be selected
appropriately according to the progress of the reaction.
Formula (23).fwdarw.Formula (24)
Formula (28).fwdarw.Formula (29) 1-(ii)
[0422] An aromatic carboxamide derivative having an amino group
represented by Formula (24) or Formula (29) can be derived from the
aromatic carboxamide derivative having a nitro group represented by
Formula (23) or Formula (28) by means of a reduction reaction.
Examples of such reduction include a method using a hydrogenation
reaction and a method using a metal compound (for example, stannous
chloride (anhydride), iron powder, zinc powder, and the like).
[0423] The reaction of the former method can be carried out in a
suitable solvent in the presence of a catalyst at normal pressure
or a higher pressure under a hydrogen atmosphere. Examples of the
catalyst may include palladium catalysts such as palladium-carbon
and the like, nickel catalysts such as Raney-nickel and the like,
cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum
catalysts, and the like, and examples of the solvent may include
water; alcohols such as methanol, ethanol, and the like; aromatic
hydrocarbons such as benzene, toluene, and the like; chained or
cyclic ethers such as ether, dioxane, tetrahydrofuran, and the
like; and esters such as ethyl acetate and the like. The pressure
may be appropriately selected within a range of 0.1 MPa to 10 MPa,
the reaction temperature may be appropriately selected within a
range of -20.degree. C. to the reflux temperature of the solvent
used, and the reaction time may be appropriately selected within a
range of several minutes to 96 hours, whereby the compound of
Formula (24) or Formula (29) can be efficiently prepared.
[0424] Examples of the latter method include a method using
stannous chloride (anhydride) as a metal compound under the
conditions described in "Organic Syntheses" Coll. Vol. III, P.
453.
Formula (24)+Formula (26).fwdarw.Formula (25) 1-(iii)
[0425] An aromatic carboxamide or carbamate derivative represented
by Formula (25) can be prepared by reacting the aromatic amine
derivative represented by Formula (24) with the carboxylic acid
derivative or the carbonate ester derivative having a leaving group
represented by Formula (26) in a suitable solvent. In the present
step, a suitable base or solvent can be used, and as the base or
solvent, those exemplified in 1-(i) can be used. Examples of the
reaction temperature, the reaction time, and the like may include
those exemplified in 1-(i).
[0426] In Formula (26), the carbonyl chloride derivative can be
prepared easily from a carboxylic acid derivative by a general
method using a halogenating agent. The halogenating agent may
include those exemplified in 1-(i).
[0427] There may be a method for producing a compound represented
by Formula (25) from the carboxylic acid derivative (26) and the
compound represented by Formula (24) without the use of a
halogenating agent, and the preparation can be conducted according
to the method exemplified in 1-(i).
Formula (25)+Formula (27).fwdarw.Formula (1) 1-(iv)
[0428] The compound represented by Formula (1) of the present
invention can be prepared by reacting the amide compound
represented by Formula (25) with the compound having a leaving
group such as halogen and the like, represented by Formula (27) in
a solvent or without a solvent. In the present step, a suitable
base or solvent can be used, and as the base or solvent, those
exemplified in 1-(i) can be used. Examples of the reaction
temperature, the reaction time, and the like may include those
exemplified in 1-(i).
Formula (28)+Formula (30).fwdarw.Formula (23) 1-(v)
[0429] A compound represented by Formula (23) can be prepared by
reacting the amide compound represented by Formula (28) with the
compound having a leaving group such as halogen and the like,
represented by Formula (30) in a solvent or without a solvent. In
the present step, a suitable base or solvent can be used, and as
the base or solvent, those exemplified in 1-(i) can be used.
Examples of the reaction temperature, the reaction time, and the
like may include those exemplified in 1-(i).
Formula (29).fwdarw.Formula (31) 1-(vi)
[0430] (Method A)
[0431] A compound represented by Formula (31) can be prepared by
reacting the compound represented by Formula (29) with an aldehyde
or a ketone in a solvent, and reacting them under a hydrogen
atmosphere with the addition of a catalyst.
[0432] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as
1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide,
methanol, ethanol, and the like, and water. These solvents may be
used alone or as a mixture of two or more kinds thereof.
[0433] Examples of the catalyst may include palladium catalysts
such as palladium-carbon, palladium hydroxide-carbon, and the like,
nickel catalysts such as Raney-nickel and the like, cobalt
catalysts, platinum catalysts, ruthenium catalysts, rhodium
catalysts, and the like.
[0434] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, trifluoroacetaldehyde,
difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde,
dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde, and
the like.
[0435] Examples of the ketones may include acetone,
perfluoroacetone, methyl ethyl ketone, and the like.
[0436] The reaction pressure may be appropriately selected within
the range of 1 atm to 100 atm. The reaction temperature may be
appropriately selected within the range from -20.degree. C. to the
reflux temperature of the solvent used. Further, the reaction time
may be appropriately selected within the range from several minutes
to 96 hours.
[0437] (Method B)
[0438] A compound represented by Formula (31) can be prepared by
reacting the compound represented by Formula (29) with an aldehyde
or a ketone in a solvent, and treating the product with a reducing
agent.
[0439] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as
1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide,
methanol, ethanol, and the like, water, and the like. These
solvents may be used alone or as a mixture of two or more kinds
thereof.
[0440] Examples of the reducing agent may include, for example,
borohydrides such as sodium borohydride, sodium cyanoborohydride,
sodium triacetate borohydride, and the like.
[0441] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, trifluoroacetaldehyde,
difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde,
dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde, and
the like.
[0442] Examples of the ketones may include acetone,
perfluoroacetone, methyl ethyl ketone, and the like.
[0443] The reaction temperature may be appropriately selected
within the range from -20.degree. C. to the reflux temperature of
the solvent used. Further, the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
[0444] (Method C)
[0445] A compound of Formula (31) can be prepared by reacting the
compound represented by Formula (29) with an aldehyde in a solvent
or without a solvent.
[0446] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as
1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide,
methanol, ethanol, and the like, inorganic acids such as sulfuric
acid, hydrochloric acid, and the like, organic acids such as formic
acid, acetic acid, and the like, water, and the like. These
solvents may be used alone or as a mixture of two or more kinds
thereof.
[0447] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, and the like.
[0448] The reaction temperature may be appropriately selected
within the range from -20.degree. C. to the reflux temperature of
the solvent used, and the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
Formula (31)+Formula (26).fwdarw.General Formula (32) 1-(vii)
[0449] An aromatic carboxamide or carbamate derivative represented
by Formula (32) can be prepared by reacting the aromatic amine
derivative represented by Formula (31) with the carboxylic acid
derivative or the carbonate ester derivative having a leaving group
represented by Formula (26) in a suitable solvent. In the present
step, a suitable base or solvent can be used, and as the base or
solvent, those exemplified in 1-(i) can be used. Examples of the
reaction temperature, the reaction time, and the like may include
those exemplified in 1-(i).
[0450] In Formula (26), the carbonyl chloride derivative can be
prepared easily from a carboxylic acid derivative by a general
method using a halogenating agent. The halogenating agent may
include those exemplified in 1-(i).
[0451] There may be exemplified a method for producing a compound
represented by Formula (32) from the carboxylic acid derivative
(26) and the compound represented by Formula (31) without the use
of a halogenating agent, and the preparation can be conducted
according to the method exemplified in 1-(i).
Formula (32)+Formula (30).fwdarw.Formula (1) 1-(viii)
[0452] The compound represented by Formula (1) of the present
invention can be prepared by reacting the amide compound
represented by Formula (32) with the compound having a leaving
group such as a halogen and the like, represented by Formula (30)
in a solvent or without a solvent. In the present step, a suitable
base or solvent can be used, and as the base or solvent, those
exemplified in 1-(i) can be used. Examples of the reaction
temperature, the reaction time, and the like may include those
exemplified in 1-(i).
[0453] <Preparation Method 2>
##STR00115## Formula (33)+Formula (22).fwdarw.Formula (34)
2-(i)
[0454] A compound represented by Formula (34) can be prepared by
reacting the compound represented by Formula (33) with a compound
represented by Formula (22) under the condition described in
1-(i).
Formula (34).fwdarw.Formula (36) 2-(ii)
[0455] A compound represented by Formula (36) can be prepared by
carrying out an amination reaction using an amination agent such as
ammonia and the like according to the conditions described, for
example, in J. Org. Chem. p. 280 (1958). However, the conditions
such as a reaction solvent and the like are not restricted to those
described in the literature, and an inert solvent which does not
inhibit the proper progress of the reaction significantly may be
used. The reaction temperature and reaction time may be suitably
selected as the reaction proceeds. Further, examples of the
amination agent include methylamine, ethylamine or the like, in
addition to ammonia.
Formula (36)+Formula (26).fwdarw.Formula (1) 2-(iii)
[0456] The compound represented by Formula (1) can be prepared by
reacting the compound represented by Formula (36) with a compound
represented by Formula (26) according to the conditions described
in 1-(i).
[0457] <Preparation Method 3>
##STR00116## Formula (29)+Formula (26).fwdarw.Formula (35)
3-(i)
[0458] An aromatic carboxamide or carbamate derivative represented
by Formula (35) can be prepared by reacting the aromatic amine
derivative represented by Formula (29) with the carboxylic acid
derivative or the carbonate ester derivative having a leaving group
represented by Formula (26) in a suitable solvent. In the present
step, a suitable base or solvent can be used, and as the base or
solvent, those exemplified in 1-(i) can be used. Examples of the
reaction temperature, the reaction time, and the like may include
those exemplified in 1-(i).
[0459] In Formula (26), the carbonyl chloride derivative can be
prepared easily from a carboxylic acid derivative by a general
method using a halogenating agent. The halogenating agent may
include those exemplified in 1-(i).
[0460] There may be exemplified a method for producing a compound
represented by Formula (35) from the carboxylic acid derivative
(26) and the compound represented by Formula (29) without the use
of a halogenating agent, and the preparation can be conducted
according to the method exemplified in 1-(i).
Formula (35)+Formula (27).fwdarw.Formula (1a) 3-(ii)
[0461] The compound represented by Formula (1a) of the present
invention can be prepared by reacting the amide compound
represented by Formula (35) with the compound having a leaving
group such as halogen and the like, represented by Formula (27) in
a solvent or without a solvent. In the present step, a suitable
base or solvent can be used, and as the base or solvent, those
exemplified in 1-(i) can be used. Examples of the reaction
temperature, the reaction time, and the like may include those
exemplified in 1-(i).
[0462] <Preparation Method 4>
##STR00117## Formula (24).fwdarw.Formula (36) 4-(i)
[0463] A compound represented by Formula (36) can be prepared by
reacting the compound represented by Formula (24) as a starting
material according to the conditions of (Method A), (Method B), or
(Method C) described in 1-(vi).
Formula (24)+Formula (27).fwdarw.Formula (36) 4-(i')
[0464] An aromatic carboxamide represented by Formula (36) can be
prepared by reacting the aromatic amine derivative represented by
Formula (24) with the carboxylic acid derivative or the carbonate
ester derivative having a leaving group represented by Formula (27)
in a suitable solvent. In the present step, a suitable base or
solvent can be used, and as the base or solvent, those exemplified
in 1-(i) can be used. Examples of the reaction temperature, the
reaction time, and the like may include those exemplified in
1-(i).
[0465] In Formula (27), the carbonyl chloride derivative can be
prepared easily from a carboxylic acid derivative by a general
method using a halogenating agent. The halogenating agent may
include those exemplified in 1-(i).
[0466] There may be exemplified a method for producing a compound
represented by Formula (36) from the carboxylic acid derivative
(27) and the compound represented by Formula (24) without the use
of a halogenating agent, and the preparation can be conducted
according to the method exemplified in 1-(i).
Formula (36)+Formula (26).fwdarw.Formula (1) 4-(ii)
[0467] A compound represented by Formula (1) can be prepared by
reacting the compound represented by Formula (36) and the compound
represented by Formula (26) as starting materials according to the
conditions described in 1-(i).
[0468] <Preparation Method 5>
##STR00118## Formula (37)+Formula (22).fwdarw.Formula (38)
5-(i)
[0469] A compound represented by Formula (38) can be prepared by
reacting the compound represented by Formula (37) and the compound
represented by Formula (22) according to the conditions described
in 1-(i).
Formula (38).fwdarw.Formula (39) 5-(ii)
[0470] A compound represented by Formula (39) can be prepared by
reacting the nitro aromatic carboxamide derivative represented by
Formula (38) with a suitable fluorinating agent in a suitable
solvent or without a solvent.
[0471] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, toluene, xylene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, chained or cyclic ethers such as
diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and
the like, esters such as ethyl acetate, butyl acetate, and the
like, ketones such as acetone, methyl isobutyl ketone,
cyclohexanone, methyl ethyl ketone, and the like, nitriles such as
acetonitrile, propionitrile, and the like, and aprotic polar
solvents such as 1,3-dimethyl-2-imidazolidinone, sulfolane,
dimethylsulfoxide, N,N-dimethyl formamide, N-methylpyrrolidone,
N,N-dimethylacetamide, and the like. These solvents may be used
alone or as a mixture of two or more kinds thereof.
[0472] Examples of the fluorinating agent may include
1,1,2,2-tetrafluoroethyl diethylamine,
2-chloro-1,1,2-trifluoroethyl diethylamine,
trifluorodiphenylphospholane, difluorotriphenylphospholane,
fluoroformic acid esters, sulfur tetrafluoride, potassium fluoride,
potassium hydrogen fluoride, cesium fluoride, rubidium fluoride,
sodium fluoride, lithium fluoride, antimony (III) fluoride,
antimony (V) fluoride, zinc fluoride, cobalt fluoride, lead
fluoride, copper fluoride, mercury (II) fluoride, silver fluoride,
silver fluoroborate, thallium (I) fluoride, molybdenum (VI)
fluoride, arsenic (III) fluoride, bromine fluoride, selenium
tetrafluoride, tris(dimethylamino)sulfonium
difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary
ammonium fluorides, (2-chloroethyl) diethylamine,
diethylaminosulfur trifluoride, morpholinosulfur trifluoride,
silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid,
hydrogen fluoride-pyridine complex, hydrogen fluoride-triethylamine
complex, hydrogen fluoride salts, bis(2-methoxyethyl)amino
sulfurtrifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone,
iodine pentafluoride, tris(diethylamino)phosphonium
2,2,3,3,4,4-hexafluorocyclobutanilide, triethylammonium
hexafluorocylcobutanilide, hexafluoropropene, and the like. These
fluorinating agents may be used alone or as a mixture of two or
more kinds thereof.
[0473] The fluorinating agent may be appropriately selected and
used as a solvent, in the range of 1-fold molar equivalent to
10-fold molar equivalents with respect to the nitro aromatic
carboxamide derivative represented by Formula (38).
[0474] Additives may be used, and examples thereof may include
crown ethers such as 18-crown-6 and the like, phase transfer
catalysts such as a tetraphenylphosphonium salt and the like,
inorganic salts such as calcium fluoride, calcium chloride, and the
like, metal oxides such as mercury oxide and the like, ion exchange
resins, and the like. These additives may not only be added to the
reaction system but also used as a pretreating agent for the
fluorinating agent.
[0475] The reaction temperature may be appropriately selected
within the range from -80.degree. C. to the reflux temperature of
the solvent used, and the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
[0476] <Preparation Method 6>
##STR00119## Formula (40)+Formula (22).fwdarw.Formula (41)
6-(i)
[0477] A compound represented by Formula (41) can be prepared by
reacting the compound represented by Formula (40) with a compound
represented by Formula (22) according to the conditions described
in 1-(i).
Formula (41).fwdarw.Formula (42) 6-(ii)
[0478] A compound represented by Formula (42) can be prepared by
reacting the halogen aromatic carboxamide derivative represented by
Formula (41) with a suitable cyanating agent in a suitable solvent
or without a solvent.
[0479] The solvent may be any of those which do not inhibit the
progress of the present reaction significantly. Examples thereof
may include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, toluene, xylene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, chained or cyclic ethers such as
diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and
the like, esters such as ethyl acetate, butyl acetate, and the
like, ketones such as acetone, methyl isobutyl ketone,
cyclohexanone, methyl ethyl ketone, and the like, nitriles such as
acetonitrile, propionitrile, and the like, and aprotic polar
solvents such as 1,3-dimethyl-2-imidazolidinone, sulfolane,
dimethylsulfoxide, N,N-dimethyl formamide, N-methylpyrrolidone,
N,N-dimethylacetamide, and the like. These solvents may be used
alone or as a mixture of two or more kinds thereof.
[0480] Examples of the cyanating agent include cyanide salts such
as sodium cyanide, potassium cyanide, sodium cyanoborohydride, and
the like, metal cyanides such as copper cyanide, silver cyanide,
lithium cyanide, and the like, hydrogen cyanide, tetraethylammonium
cyanide, and the like.
[0481] These cyanating agents may be appropriately selected and
used in the range of 1-fold molar equivalent to 10-fold molar
equivalents with respect to the halogen aromatic carboxamide
derivative represented by Formula (41).
[0482] Additives may be used, and examples thereof may include
crown ethers such as 18-crown-6 and the like, phase transfer
catalysts such as a tetraphenylphosphonium salt and the like,
inorganic salts such as sodium iodide and the like.
[0483] The reaction temperature may be appropriately selected
within the range from -20.degree. C. to the reflux temperature of
the solvent used. Further, the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
[0484] <Preparation Method 7>
##STR00120## Formula (43).fwdarw.Formula (44) 7-(i)
[0485] A compound represented by Formula (44) can be prepared by
reacting the compound represented by Formula (43) with a Lawesson's
reagent according to the known conditions described in Synthesis p.
463 (1993), Synthesis p. 829 (1984) and the like. The conditions
such as a solvent, reaction temperature and the like are not
restricted to those described in the literature.
Formula (44)+Formula (26).fwdarw.Formula (45) 2-(ii)
[0486] A compound represented by Formula (45) can be prepared by
reacting the compound represented by Formula (44) with a compound
represented by Formula (26) according to the conditions described
in 1-(i).
[0487] <Preparation Method 8>
##STR00121## Formula (46).fwdarw.Formula (47)+Formula (48) 8
[0488] The compounds represented by Formula (47) and Formula (48)
can be prepared from a compound represented by Formula (46)
according to the conditions described in 7-(i). The conditions such
as a solvent, a reaction temperature, and the like are not
restricted to those described in the literature. These two
compounds can be easily separated and purified by a known
separation and purification technique such as silica gel column
chromatography and the like.
[0489] <Preparation Method 9>
##STR00122## Formula (49)+Formula (26).fwdarw.Formula (50)
9-(i)
[0490] Carboxylic acids having an acylamino group represented by
Formula (50) can be prepared by reacting a carboxylic acid having
an amino group represented by Formula (49) as a starting material
with a compound represented by Formula (26) according to the
conditions described in 1-(i).
Formula (50).fwdarw.Formula (51) 9-(ii)
[0491] A compound represented by Formula (51) can be prepared by a
known general method including reacting the compound represented by
Formula (50) with thionyl chloride, oxalyl chloride, phosgene,
phosphorus oxychloride, phosphorus pentachloride, phosphorus
trichloride, thionyl bromide, phosphorus tribromide,
diethylaminosulfur trifluoride, or the like.
Formula (51)+Formula (22).fwdarw.Formula (1) 9-(iii)
[0492] The compound represented by Formula (1) can be prepared by
reacting a compound represented by Formula (51) with a compound
represented by Formula (22) according to the conditions described
in 1-(i).
Formula (50)+Formula (22).fwdarw.Formula (1) 9-(iv)
[0493] The compound represented by Formula (1) can be prepared by
reacting the compound represented by Formula (50) with a compound
represented by Formula (22) according to the condition using a
condensing agent or the condition using a mixed anhydride method
according to 1-(i).
[0494] In all of the preparation methods as described above, a
desired product may be isolated from the reaction system after the
reaction is completed according to a general method, but if
required, purification can be carried out by operations such as
recrystallization, column chromatography, distillation, and the
like. In addition, the desired product can be also provided to the
subsequent reaction process without being separated from the
reaction system.
[0495] Hereinbelow, examples of the representative compounds of the
amide derivative represented by Formula (1), Formula (7), or
Formula (8) as an active ingredient for the pest control agent of
the present invention will be given in Table 1 to Table 51 below,
but the present invention is not limited thereto.
[0496] In addition, in the tables, "n-" represents normal, "i-"
represents iso, "s-" represents secondary, "t-" represents
tertiary, "Me" represents a methyl group, "Et" represents an ethyl
group, "n-Pr" represents a normal propyl group, "i-Pr" represents
an isopropyl group, "n-Bu" represents a normal butyl group, "i-Bu"
represents an isobutyl group, "s-Bu" represents a secondary butyl
group, "t-Bu" represents a tertiary butyl group, "CF3" represents a
trifluoromethyl group, "C2F5" represents a pentafluoroethyl group,
"n-C3F7" represents a heptafluoronormal propyl group, "i-C3F7"
represents a heptafluoroisopropyl group, "OCF3" represents a
trifluoromethoxy group, "OC2F5" represents a pentafluoroethoxy
group, "H" represents a hydrogen atom, "F" represents a fluorine
atom, "Cl" represents a chlorine atom, "Br" represents a bromine
atom, "I" represents an iodine atom, "O" represents an oxygen atom,
"C(O)" represents a carbonyl group, "CN" represents a cyano group,
"Py" represents a pyridyl group, "Ph" represents a phenyl group,
and "S(O)2" represents a sulfonyl group, respectively.
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[0497] Hereinbelow, Table 52 shows the physical properties of the
representative compounds of the amide derivative of the present
invention. The .sup.1H-NMR chemical shift values shown therein are
based on tetramethylsilane as an internal standard substance unless
specified otherwise.
TABLE-US-00052 TABLE 52 compound number .sup.1H-NMR (CDCl.sub.3,
ppm) 1-470 .delta. 7.55-7.68 (3H, m), 7.80-7.99 (6H, m), 8.58 (1H,
s), 8.61 (1H, s), 9.12 (1H, d, J = 1.5 Hz). 1-491 .delta. 7.34-7.91
(4H, m), 8.00 (1H, s), 8.08 (2H, dd, J = 1.9, 6.8 Hz), 8.00 (1H,
s), 8.49 (1H, s), 8.59 (1H, s), 9.04 (1H, s). 1-506 .delta. 7.48
(1H, dd, J = 4.9, 7.81 Hz), 7.83-7.90 (3H, m), 8.00 (1H, s), 8.31
(1H, dd, J = 1.9, 7.8 Hz), 8.34 (1H, s), 8.61 (1H, dd, J = 1.9, 4.9
Hz), 9.09 (1H, s), 9.10 (1H, s). 1-513 .delta. 7.54 (1H, d, J = 7.8
Hz), 7.83-7.90 (3H, m), 8.00 (1H, s), 8.21 (1H, dd, J = 2.4, 8.3
Hz), 8.31 (1H, s), 8.51 (1H, s), 9.00 (1H, s), 9.01 (1H, d, J = 7.8
Hz). 1-627 .delta. 7.56-7.59 (3H, m), 7.64-7.66 (1H, m), 7.80-7.87
(2H, m), 7.94-7.97 (2H, m), 8.16 (1H, s), 8.46 (1H, s), 8.57 (1H,
s), 9.16 (1H, s). 1-1925 .delta. 7.52-7.59 (2H, m), 7.65-7.71 (2H,
m), 7.93-7.95 (2H, m), 8.00-8.02 (2H, m), 8.12-8.16 (2H, m), 8.52
(1H, d, J = 11.2 Hz). 1-1968 .delta. 7.54 (1H, d J = 8.8 Hz), 7.72
(1H, d J = 8.8 Hz), 7.93 (1H, s), 8.09 (1H, s), 8.17-8.18 (2H, m),
8.27 (1H, dd, J = 2.4, 8.8 Hz), 8.38 (1H, d J = 10.8 Hz), 8.98 (1H,
d, J = 2.4 Hz). 2-491 .delta. 3.81 (3H, broad-s), 7.52-7.84 (8H,
m), 7.89 (1H, s), 8.00 (1H, s). 2-513 .delta. 3.58 (3H, s),
7.34-7.36 (1H, m), 7.81-8.00 (8H, m). 2-518 .delta. 3.59 (3H, s),
7.69 (1H, broad-s), 7.81-8.01 (7H, m), 8.50 (1H, broad-s). 6-38
.delta. 7.51-7.62 (4H, m), 7.75-8.00 (8H, m), 8.32 (1H, s). 6-39
.delta. 7.22 (1H, dd, J = 8.0, 12.4 Hz), 7.32-7.36 (1H, m),
7.51-7.55 (2H, m), 7.78 (1H, d, J = 7.6 Hz), 7.86-7.90 (3H, m),
8.11 (1H, s), 8.17-8.18 (1H, m), 8.35 (1H, s), 8.62-8.67 (1H, m).
6-45 .delta. 7.57-7.59 (1H, m), 7.65-7.69 (1H, m), 7.77-7.79 (1H,
m), 7.89-7.9 (5H, m), 8.14-8.29 (4H, m). 6-46 .delta. 7.55-7.59
(1H, m), 7.77-8.07 (10H, m), 8.27 (1H, s). 6-47 .delta. 7.01-7.05
(2H, m), 7.44-7.56 (2H, m), 7.78-7.86 (4H, m), 8.03 (1H, s), 8.11
(1H, s), 8.33 (1H, s). 6-57 .delta. 7.28-7.32 (1H, m), 7.45-7.67
(4H, m), 7.76-8.02 (5H, m), 8.30 (1H, s). 6-60 .delta. 7.50-7.60
(2H, m), 7.78-8.02 (6H, m), 8.19-8.27 (2H, m), 8.91 (1H, s). 6-71
.delta. 7.51-7.62 (4H, m), 7.78-7.80 (1H, d, J = 8.0 Hz), 7.90-7.92
(3H, m), 8.06-8.09 (4H, m), 8.34 (1H, s). 6-72 .delta. 7.22-7.25
(1H, m), 7.35 (1H, t, J = 8.0 Hz), 7.55-7.60 (2H, m), 7.80 (1H, d,
J = 8.0 Hz), 7.92 (1H, d, J = 8.0 Hz), 8.01 (1H, s), 8.10 (2H, s),
8.20 (1H, t, J = 8.0 Hz), 8.37 (1H, s), 8.65 (1H, d, J = 16.8 Hz).
6-78 .delta. 7.58 (1H, t, J = 7.8 Hz), 7.68 (1H, t, J = 7.8), 7.80
(1H, d, J = 8.0 Hz), 7.87 (1H, d, 8.0 Hz), 7.95 (1H, d, J = 8.0
Hz), 8.00 (1H, s), 8.09 (2H, s), 8.15 (1H, d, J = 8.0 Hz), 8.23
(1H, s), 8.26 (1H, s), 8.30 (1H, s). 6-79 .delta. 7.58 (1H, t, J =
8.2 Hz), 7.79-7.83 (3H, m), 7.97 (2H, s), 8.01 (2H, d, J = 8.0 Hz),
8.09 (2H, s), 8.18 (1H, s), 8.29 (1H, s). 6-80 .delta. 7.05 (2H, t,
J = 8.2 Hz), 7.48 (1H, t, J = 6.6 Hz), 7.56 (1H, t, J = 7.8 Hz),
7.81 (1H, d, J = 8.0 Hz), 7.89-7.91 (2H, m), 7.98 (1H, s), 8.10
(2H, s), 8.33 (1H, s). 6-90 .delta. 7.43-7.46 (1H, m), 7.59 (1H, t,
J = 7.2 Hz), 7.82 (1H, d, J = 7.2 Hz), 7.93 (2H, d, J = 9.6 Hz),
8.10 (2H, s), 8.24 (1H, d, J = 6.4 Hz), 8.33 (1H, s), 8.44 (1H, s),
8.56 (1H, s). 6-93 .delta. 7.51 (1H, d, J = 8.4 Hz), 7.59 (1H, t, J
= 7.6 Hz), 7.81 (1H, d, J = 7.6 Hz), 7.94 (2H, s), 8.10-8.11 (3H,
m), 8.20 (1H, d, J = 8.0 Hz), 8.28 (1H, s), 8.91 (1H, s). 6-111
(DMSO-d.sub.6) .delta. 7.50-7.60 (4H, m), 7.70-7.73 (1H, m),
7.93-8.00 (3H, m), 8.04-8.08 (1H, m), 8.34-8.36 (2H, m), 10.48 (1H,
s), 10.60 (1H, s). 6-147 (DMSO-d.sub.6) .delta. 7.55-7.61 (2H, m),
7.74 (1H, d, J = 7.9 Hz), 7.94-7.97 (2H, m), 8.10 (1H, dd, J = 2.0,
7.6 Hz), 8.27 (1H, s), 8.34 (1H, s), 8.54 (1H, dd, J = 2.0, 4.9
Hz), 10.65 (1H, s), 10.89 (1H, s). 6-268 .delta. 7.50-7.61 (4H, m),
7.70 (1H, d, J = 7.8 Hz), 7.85-7.92 (4H, m), 7.96-8.01 (2H, m),
8.14 (1H, s), 8.24 (1H, t, J = 2.0 Hz). 6-269 .delta. 7.22-7.25
(1H, m), 7.36 (1H, t, J = 8.0 Hz), 7.56-7.57 (2H, m), 7.75 (1H, d,
J = 8.0 Hz), 7.90-8.00 (2H, m), 8.07 (1H, s), 8.17-8.20 (2H, m),
8.33 (1H, s), 8.65 (1H, d, J = 16.4 Hz). 6-270 .delta. 7.25 (1H, t,
J = 8.0 Hz), 7.43-7.53 (2H, m), 7.77-7.81 (4H, m), 7.85 (1H, d, J =
8.0 Hz), 7.91 (1H, s), 8.13 (1H, s), 8.19 (1H, d, J = 8.0 Hz), 8.24
(1H, s). 6-271 .delta. 7.09-7.22 (2H, m), 7.55 (1H, t, J = 7.8 Hz),
7.71 (1H, d, J = 8.0 Hz), 7.89-7.93 (4H, m), 8.03 (2H, d, J = 8.0
Hz), 8.14 (1H, s), 8.23 (1H, s). 6-272 .delta. 7.40-7.50 (4H, m),
7.56 (1H, t, J = 8.0 Hz), 7.80 (2H, t, J = 8.4 Hz), 7.87 (2H, s),
7.91 (1H, d, J = 7.9 Hz), 8.09 (1H, s), 8.32 (1H, s). 6-288 .delta.
7.54-7.55 (1H, m), 7.65-7.66 (1H, m), 7.72 (1H, d, J = 7.8 Hz),
7.85 (1H, d, J = 7.8 Hz), 7.91 (1H, s), 7.95-7.98 (2H, m),
8.13-8.23 (4H, m), 8.36 (1H, s). 6-289 .delta. 7.55-7.56 (1H, m),
7.71 (1H, d, J = 7.8 Hz), 7.80 (2H, d, J = 8.3 Hz), 7.91-7.96 (3H,
m), 7.99 (2H, d, J = 8.3 Hz), 8.20 (1H, s), 8.21-8.22 (2H, m).
6-290 .delta. 7.01-7.05 (2H, m), 7.42-7.44 (1H, m), 7.55 (1H, t, J
= 8.0 Hz), 7.75 (1H, d, J = 8.0 Hz), 7.90-7.95 (3H, m), 8.01 (1H,
s), 8.14 (1H, s), 8.26 (1H, s). 6-293 .delta. 7.14 (1H, t, J = 8.0
Hz), 7.22-7.29 (2H, m), 7.54 (1H, t, J = 7.8 Hz), 7.74 (1H, d, J =
7.8 Hz), 7.84-7.88 (3H, m), 8.11 (1H, s), 8.15 (1H, s), 8.25 (1H,
s). 6-300 .delta. 7.06-7.59 (2H, m), 7.62 (1H, dd, J = 1.5, 7.8
Hz), 7.81 (1H, d, J = 7.8 Hz), 7.92 (1H, s), 8.08-8.16 (4H, m),
9.35-9.40 (1H, m), 9.51 (1H, broad-s). 6-304 .delta. 7.44 (1H, dd,
J = 4.9, 7.8 Hz), 7.58 (1H, t, J = 7.8 Hz), 7.75 (1H, d, J = 7.8
Hz), 7.81 (1H, s), 7.92-7.96 (2H, m), 8.15 (1H, s), 8.22-8.26 (2H,
m), 8.38 (1H, s), 8.55 (1H, dd, J = 2.0, 4.9 Hz). 6-306 .delta.
7.42-7.45 (1H, m), 7.58 (1H, t, J = 7.8 Hz), 7.75 (1H, d, J = 7.8
Hz), 7.88 (1H, broad-s), 7.93-7.95 (2H, m), 8.15 (1H, broad-s),
8.23 (1H, dd, J = 2.0, 7.8 Hz), 8.24 (1H, s), 8.39 (1H, broad-s),
8.55 (1H, dd, J = 2.0, 4.8 Hz). 6-311 .delta. 7.45-7.52 (1H, m),
7.74 (1H, d, J = 8.0 Hz), 7.92-7.96 (1H, m), 8.00 (1H, s), 8.14
(1H, s), 8.22-8.23 (3H, m), 8.29 (1H, d, J = 8.0 Hz), 8.91 (1H, s),
9.07 (1H, s). 6-346 .delta. 7.50-7.62 (4H, m), 7.71-7.73 (1H, m),
7.89-7.93 (4H, m), 8.02-8.04 (2H, m), 8.13 (1H, s), 8.27 (1H, s).
6-347 .delta. 7.19-7.25 (1H, m), 7.33-7.37 (1H, m), 7.52-7.59 (2H,
m), 7.73-7.75 (1H, m), 7.89-7.91 (2H, m), 8.09-8.21 (3H, m), 8.31
(1H, s), 8.65 (1H, s). 6-348 .delta. 7.30-7.31 (1H, m), 7.48-7.74
(5H, m), 7.91-7.92 (2H, m), 8.02 (1H, s), 8.07 (1H, s), 8.13 (1H,
s), 8.25 (1H, s). 6-349 .delta. 7.17-7.21 (2H, m), 7.51-7.55 (1H,
m), 7.70-7.72 (1H, m), 7.88-7.93 (4H, m), 8.04 (1H, s), 8.11-8.23
(2H, m), 8.23 (1H, s). 6-366 .delta. 7.53-7.55 (1H, m), 7.62-7.72
(2H, m), 7.84-7.94 (3H, m), 8.09-8.16 (3H, m), 8.22-8.24 (2H, m),
8.40 (1H, s). 6-367 .delta. 7.54-7.58 (1H, m), 7.72-7.74 (1H, m),
7.80-7.83 (2H, m), 7.91-7.94 (2H, m), 8.00-8.07 (2H, m), 8.13 (1H,
s), 8.18 (1H, s), 8.23 (1H, s), 8.24 (1H, s). 6-368 .delta.
7.01-7.06 (2H, m), 7.44-7.57 (3H, m), 7.74-7.76 (1H, m), 7.86-7.91
(2H, m), 8.07 (1H, s), 8.13-8.14 (1H, m), 8.28 (1H, s). 6-382
.delta. 7.43-7.46 (1H, m), 7.56-7.60 (1H, m), 7.76-7.78 (1H, m),
7.90-7.91 (2H, m), 8.02 (1H, s), 8.14 (1H, s), 8.25 (2H, s), 8.43
(1H, s), 8.54-8.56 (1H, m). 6-389 .delta. 7.30-7.60 (2H, m),
7.74-7.76 (1H, m), 7.91-7.98 (3H, m), 8.07 (1H, s), 8.14 (1H, s),
8.19-8.23 (2H, m), 8.90 (1H, s). 6-424 .delta. 7.51-7.62 (4H, m),
7.73 (1H, d, J = 8.3 Hz), 7.89-7.94 (4H, m), 8.01 (1H, s), 8.10
(1H, s), 8.27 (1H, t, J = 1.5 Hz), 8.35 (1H, s). 6-425 .delta.
7.20-7.25 (1H, m), 7.34-7.37 (1H, m), 7.54-7.58 (2H, m), 7.75 (1H,
d, J = 7.6 Hz), 7.88-7.95 (2H, m), 8.18-8.22 (2H, m), 8.33-8.34
(2H, m), 8.66 (1H, d, J = 16.4 Hz). 6-426 .delta. 7.28-7.30 (1H,
m), 7.46-7.66 (5H, m), 7.71-7.94 (2H, m), 8.11-8.24 (3H, m), 8.34
(1H, s). 6-427 .delta. 7.18-7.22 (2H, m), 7.52-7.57 (1H, m), 7.73
(1H, d, J = 7.6 Hz), 7.89-8.03 (5H, m), 8.22-8.25 (2H, m), 8.35
(1H, s). 6-428 .delta. 7.42-7.50 (4H, m), 7.56 (1H, t, J = 8.0 Hz),
7.75 (1H, d, J = 8.0 Hz), 7.81 (1H, d, J = 7.8 Hz), 7.95-7.96 (2H,
m), 8.09 (1H, s), 8.28 (1H, s), 8.36 (1H, s). 6-444 .delta. 7.56
(1H, t, J = 7.8 Hz), 7.66 (1H, t, J = 7.8 Hz), 7.73 (1H, t, J = 7.8
Hz), 7.86 (1H, dd, J = 1.5, 7.8 Hz), 7.93-7.96 (2H, m), 8.07 (1H,
s), 8.14-8.16 (1H, m), 8.22-8.26 (3H, m), 8.34 (1H, s). 6-445
.delta. 7.57 (1H, t, J = 7.8 Hz), 7.74 (1H, d, J = 7.8 Hz),
7.81-7.83 (2H, m), 7.95 (1H, s), 7.97-8.04 (4H, m), 8.12 (1H,
broad-s), 8.23 (1H, t, J = 2.0 Hz), 8.35 (1H, broad-s). 6-446
.delta. 7.01-7.05 (2H, m), 7.43-7.57 (2H, m), 7.75-7.77 (1H, m),
7.88-7.94 (3H, m), 8.13 (1H, s), 8.27 (1H, s), 8.35 (1H, s). 6-448
.delta. 7.39-7.41 (1H, m), 7.51-7.58 (2H, m), 7.74-7.78 (2H, m),
7.90-7.95 (2H, m), 8.04 (1H, s), 8.15 (1H, s), 8.26 (1H, s), 8.35
(1H, s). 6-449 .delta. 7.12-7.36 (3H, m), 7.52-7.58 (1H, m),
7.75-7.95 (4H, m), 8.21-8.35 (3H, m). 6-450 6.82-6.86 (1H, m),
7.00-7.01 (1H, m), 7.15 (1H, t, J = 7.8 Hz), 7.56 (1H, t, J = 8.2
Hz), 7.74 (1H, d, J = 8.1 Hz), 7.84 (1H, t, J = 8.8 Hz), 7.90-7.91
(1H, m), 7.95 (1H, s), 8.04 (1H, s), 8.42 (1H, s). 6-451 .delta.
7.23-7.69 (8H, m), 7.85 (1H, s), 8.04 (1H, s), 8.42 (1H, s). 6-452
.delta. 7.44 (1H, dd, J = 2.0, 8.3 Hz), 7.59 (1H, t, J = 8.3 Hz),
7.66 (1H, d, J = 8.3 Hz), 7.70 (1H, d, J = 2.0 Hz), 7.75 (1H, d, J
= 8.3 Hz), 7.86 (2H, broad-s), 7.95 (2H, broad-s), 8.24 (1H,
broad-s), 8.37 (1H, broad-s). 6-453 .delta. 7.15 (1H, dt, J = 2.4,
8.3 Hz), 7.40 (1H, dd, J = 2.4, 8.3 Hz), 7.60 (1H, t, J = 8.3 Hz),
7.68-7.74 (2H, m), 7.95-8.02 (4H, m), 8.24 (1H, s), 8.35 (1H, s).
6-454 .delta. 7.59 (1H, t, J = 7.8 Hz), 7.75 (1H, d, J = 7.8 Hz),
7.93 (1H, s), 7.95-7.99 (3H, m), 8.10 (1H, broad-s), 8.23-8.26 (2H,
m), 8.36 (2H, d, J = 1.9 Hz). 6-460 .delta. 7.43-7.46 (1H, m), 7.58
(1H, t, J = 7.8 Hz), 7.77 (1H, d, J = 7.8 Hz), 7.91-7.95 (2H, m),
8.01 (1H, s), 8.24 (1H, dd, J = 2.0, 7.8 Hz), 8.28 (1H, s), 8.36
(1H, s), 8.41 (1H, s), 8.54-8.56 (1H, m). 6-461 .delta. 7.45 (1H,
dd, J = 4.9, 7.3 Hz), 7.59 (1H, t, J = 7.8 Hz), 7.77 (1H, d, J =
7.8 Hz), 7.92-7.99 (3H, m), 8.24-8.29 (2H, m), 8.36-8.39 (2H, m),
8.55 (1H, dd, J = 2.0, 4.9 Hz). 6-467 .delta. 7.45-7.60 (2H, m),
7.74 (1H, d, J = 8.0 Hz), 7.95-7.97 (2H, m), 8.03 (1H, s), 8.12
(1H, s), 8.19-8.35 (2H, m), 8.35 (1H, s), 8.90 (1H, s). 6-502
.delta. 7.51-7.62 (4H, m), 7.73 (1H, d, J = 7.6 Hz), 7.89-7.95 (4H,
m), 8.01 (2H, d, J = 14.4 Hz), 8.27 (1H, s), 8.34 (1H, s). 6-503
.delta. 7.20-7.23 (1H, m), 7.34 (1H, t, J = 7.8 Hz), 7.54-7.60 (2H,
m), 7.74 (1H, d, J = 7.8 Hz), 7.94 (2H, s), 8.05 (1H, s), 8.19 (1H,
t, J = 7.8 Hz), 8.33 (2H, d, J = 12.0 Hz), 8.65 (1H, d, J = 16.0
Hz). 6-504 .delta. 7.47-7.69 (5H, m), 7.73 (1H, d, J = 7.8 Hz),
7.93 (2H, s), 8.05 (2H, d, J = 11.0 Hz), 8.25 (1H, s), 8.34 (1H,
s). 6-505 .delta. 7.20 (2H, t, J = 7.8 Hz), 7.56 (1H, t, J = 8.0
Hz), 7.73 (1H, d, J = 8.2 Hz), 7.91-7.94 (5H, m), 8.02 (1H, s),
8.24 (1H, s), 8.35 (1H, s). 6-522 .delta. 7.68-7.75 (2H, m), 7.86
(1H, d, J = 8.2 Hz), 7.93-7.96 (2H, m), 8.08 (1H, s), 8.14 (1H, d,
J = 8.0 Hz), 8.24 (2H, d, J = 8.2 Hz), 8.28 (1H, s), 8.33 (1H, s),
8.62 (1H, s). 6-523 .delta. 7.57 (1H, t, J = 7.8 Hz), 7.82 (2H, d,
J = 8.0 Hz), 7.93-8.02 (6H, m), 8.14 (1H, s), 8.23 (1H, s), 8.34
(1H, s). 6-524 .delta. 7.05 (2H, t, J = 8.0 Hz), 7.43-7.50 (1H, m),
7.56 (1H, t, J = 8.0 Hz), 7.75 (1H, d, J = 7.8 Hz), 7.86 (1H, s),
7.92 (2H, d, J = 8.2 Hz), 8.00 (1H, s), 8.27 (1H, s), 8.34 (1H, s).
6-538 .delta. 7.45 (1H, t, J = 7.6 Hz), 7.59 (2H, s), 7.70 (1H, d,
J = 4.0 Hz), 7.93 (2H, d, J = 7.6 Hz), 7.98 (1H, s), 8.28 (1H, s),
8.34 (2H, d, J = 7.6 Hz), 8.41 (1H, s). 6-545 .delta. 7.56-7.60
(1H, m), 7.75 (1H, d, J = 8.0 Hz), 7.92-8.00 (4H, m), 8.09 (1H, s),
8.19-8.23 (2H, m), 8.35 (1H, s), 8.90 (1H, s). 6-804 .delta.
7.50-7.62 (4H, m), 7.68-7.70 (1H, m), 7.85-7.91 (3H, m), 8.10 (1H,
s), 8.16-8.22 (4H, m). 6-824 .delta. 7.55-7.59 (2H, m), 7.66-7.76
(2H, m), 7.86-7.92 (2H, m), 7.99-8.08 (2H, m), 8.13-8.22 (2H, m),
8.39-8.43 (2H, m). 6-825 .delta. 7.55-7.59 (2H, m), 7.66-7.70 (2H,
m), 7.72-7.73 (2H, m), 7.86-7.92 (2H, m), 7.99-8.22 (3H, m),
8.40-8.42 (1H, m). 6-840 .delta. 7.42-7.45 (1H, m), 7.55-7.59 (1H,
t, J = 7.8 Hz), 7.71-7.30 (1H, d, J = 7.8 Hz), 7.88-7.91 (1H, m),
8.00 (1H, s), 8.20-8.24 (4H, m), 8.41 (1H, s), 8.54-8.55 (1H, m).
6-1104 .delta. 7.40 (1H, t, J = 7.8 Hz), 7.53-7.64 (3H, m), 7.89
(2H, s), 7.90-7.95 (3H, m), 8.11-8.14 (2H, m), 8.69-8.70 (1H, m).
6-1105 .delta. 7.22-7.26 (1H, m), 7.35-7.41 (2H, m), 7.58 (1H, d, J
= 8.0 Hz), 7.88-7.92 (3H, m), 8.15-8.25 (2H, m), 8.74-8.75 (2H, m).
6-1106 .delta. 7.35-7.34 (1H, m), 7.417.42 (1H, m), 7.53-7.54 (1H,
m), 7.67-7.68 (2H, m), 7.89-7.90 (3H, m), 8.09-8.10 (2H, m),
8.66-8.68 (1H, m). 6-1107 .delta. 7.21-7.26 (2H, m), 7.39-7.41 (1H,
m), 7.89-7.96 (4H, m), 8.05-8.13 (3H, m), 8.70-8.72 (1H, m). 6-1124
.delta. 7.42-7.43 (1H, m), 7.70-7.72 (1H, m), 7.89-7.92 (4H, m),
8.09-8.17 (3H, m), 8.22 (1H, s), 8.62-8.63 (1H, m). 6-1125 .delta.
7.42-7.44 (1H, m), 7.84-7.94 (5H, m), 8.02-8.11 (4H, m), 8.63-8.64
(1H, m). 6-1126 .delta. 7.05-7.09 (2H, m), 7.38-7.42 (1H, m),
7.49-7.50 (1H, m), 7.88-7.99 (4H, m), 8.09-8.12 (1H, m),
8.71-8.72 (1H, m). 6-1140 .delta. 7.40-7.49 (2H, m), 7.89 (2H, s),
7.94-7.96 (1H, m), 8.13 (1H, d, J = 12.7 Hz), 8.32-8.34 (1H, m),
8.57-8.59 (1H, m), 8.67-8.71 (1H, m), 8.75 (1H, broad-s). 6-1147
.delta. 7.39-7.44 (1H, m), 7.52-7.55 (1H, m), 7.89 (1H, s),
7.96-7.98 (1H, m), 8.05-8.11 (3H, m), 8.21-8.23 (1H, m), 8.61-8.62
(1H, m), 8.93 (1H, s). 6-1182 .delta. 7.37-7.41 (1H, m), 7.53-7.64
(3H, m), 7.87-7.94 (5H, m), 8.11-8.14 (2H, m), 8.67-8.71 (1H, m).
6-1183 .delta. 7.35-7.41 (2H, m), 7.58-7.61 (1H, m), 7.86-7.92 (3H,
m), 8.17-8.25 (2H, m), 8.61 (1H, s), 8.74 (1H, t, J = 7.8 Hz),
8.90-8.93 (1H, m). 6-1184 .delta. 7.33 (1H, t, J = 8.0 Hz), 7.40
(1H, t, J = 7.8 Hz), 7.50-7.56 (1H, m), 7.64-7.69 (2H, m), 7.88
(2H, s), 7.92 (1H, t, J = 7.8 Hz), 8.09-8.12 (2H, m), 8.63 (1H, t,
J = 8.2 Hz). 6-1185 .delta. 7.22 (2H, t, J = 7.8 Hz), 7.29-7.30
(1H, m), 7.40 (1H, t, J = 8.0 Hz), 7.88 (2H, s), 7.90-7.97 (2H, m),
8.05 (1H, s), 8.10-8.13 (1H, m), 8.64 (1H, t, J = 7.8 Hz). 6-1202
.delta. 7.42-7.44 (1H, m), 7.68-7.72 (1H, m), 7.88-7.94 (4H, m),
8.10-8.23 (4H, m), 8.60-8.65 (1H, m). 6-1203 .delta. 7.39-7.44 (1H,
m), 7.84-7.88 (4H, m), 7.92-7.95 (1H, m), 8.02-8.13 (4H, m),
8.61-8.65 (1H, m). 6-1204 .delta. 7.05 (2H, t, J = 8.0 Hz), 7.40
(1H, t, J = 8.0 Hz), 7.48-7.52 (1H, m), 7.87 (2H, s), 7.92 (1H, t,
J = 8.0 Hz), 8.01 (1H, s), 8.11-8.14 (1H, m), 8.68 (1H, t, J = 7.4
Hz). 6-1218 .delta. 7.40-7.49 (2H, m), 7.95 (2H, s), 7.94 (1H, t, J
= 7.8 Hz), 8.12-8.16 (1H, m), 8.34 (1H, d, J = 8.0 Hz), 8.58 (1H,
s), 8.70 (1H, t, J = 7.8 Hz), 8.77 (1H, s). 6-1225 .delta. 7.42
(1H, t, J = 8.2 Hz), 7.53 (1H, d, J = 8.0 Hz), 7.88 (2H, s), 7.94
(1H, t, J = 7.0 Hz), 8.06 (1H, s), 8.09-8.12 (1H, m), 8.20-8.23
(1H, m), 8.60 (1H, t, J = 8.0 Hz), 8.93 (1H, s). 6-1260 .delta.
7.39 (1H, t, J = 7.8 Hz), 7.52-7.57 (4H, m), 7.60-7.63 (2H, m),
7.93-7.94 (4H, m), 8.70 (1H, t, J = 6.3 Hz). 6-1261 .delta.
7.22-7.28 (1H, m), 7.35-7.42 (2H, m), 7.59-7.61 (1H, m), 7.94-7.95
(1H, m), 8.12 (2H, s), 8.15-8.25 (2H, m), 8.78 (1H, t, J = 1.5 Hz),
9.00 (1H, d, J = 7.8 Hz). 6-1262 .delta. 7.30-7.33 (1H, m),
7.40-7.44 (1H, m), 7.52-7.55 (2H, m), 7.64-7.70 (3H, m), 7.95-7.96
(1H, m), 8.09-8.13 (2H, m), 8.67-8.68 (1H, m). 6-1263 .delta.
7.20-7.26 (3H, m), 7.38-7.42 (1H, m), 7.91-7.98 (3H, m), 8.07-8.12
(3H, m), 8.63-8.67 (1H, m). 6-1280 .delta. 7.41-7.45 (1H, m),
7.68-7.72 (1H, m), 7.90-7.99 (2H, m), 8.08-8.25 (5H, m), 8.22-8.24
(1H, m), 8.56-8.65 (1H, m). 6-1281 .delta. 7.41-7.50 (1H, m),
7.86-7.87 (2H, m), 7.95-7.98 (1H, m), 8.03-8.13 (6H, m), 8.65-8.67
(1H, m). 6-1282 .delta. 7.06 (2H, t, J = 8.3 Hz), 7.38-7.42 (1H,
m), 7.47-7.52 (1H, m), 7.93-7.97 (1H, m), 8.01 (1H, s), 8.11-8.13
(3H, m), 8.68-8.72 (1H, m). 6-1296 .delta. 7.41-7.52 (2H, m),
7.96-8.00 (1H, m), 8.12-8.14 (3H, m), 8.33-8.35 (1H, m), 8.57-8.59
(1H, m), 8.68-8.76 (2H, m). 6-1303 .delta. 7.41-7.45 (1H, m),
7.51-7.54 (1H, m), 7.96-7.99 (1H, m), 8.06-8.24 (5H, m), 8.61 (1H,
m), 8.94 (1H, m). 6-1338 .delta. 7.38-7.42 (1H, m), 7.52-7.64 (3H,
m), 7.90-7.94 (3H, m), 8.11-8.15 (4H, m), 8.67-8.71 (1H, m). 6-1339
.delta. 7.35-7.42 (2H, m), 7.60 (1H, d, J = 8.0 Hz), 7.94 (1H, t, J
= 8.0 Hz), 8.11 (2H, s), 8.17-8.25 (2H, m), 8.62 (1H, s), 8.74 (1H,
t, J = 7.4 Hz), 8.92 (1H, d, J = 16.4 Hz). 6-1340 .delta. 7.28-7.35
(2H, m), 7.40 (1H, t, J = 8.0 Hz), 7.51-7.56 (1H, m), 7.64-7.70
(2H, m), 7.94 (1H, t, J = 8.0 Hz), 8.10 (2H, s), 8.14 (1H, s), 8.65
(1H, t, J = 8.0 Hz). 6-1341 .delta. 7.20-7.25 (2H, m), 7.40 (1H, t,
J = 8.0 Hz), 7.92-7.97 (3H, m), 8.09 (1H, d, J = 8.0 Hz), 8.11 (2H,
s), 8.14 (1H, s), 8.64 (1H, t, J = 8.0 Hz). 6-1358 .delta.
7.41-7.45 (1H, m), 7.68-7.72 (1H, m), 7.89-7.98 (2H, m), 8.10-8.23
(6H, m), 8.60-8.64 (1H, m). 6-1359 .delta. 7.41-7.45 (1H, m),
7.83-7.89 (2H, m), 7.94-7.99 (1H, m), 8.03-8.14 (6H, m), 8.62-8.66
(1H, m). 6-1360 .delta. 7.05 (1H, t, J = 8.8 Hz), 7.41-7.46 (1H,
m), 7.52 (1H, t, J = 7.8 Hz), 7.95 (1H, t, J = 7.8 Hz), 8.03 (1H,
s), 8.10 (2H, s), 8.15 (1H, s), 8.61 (1H, s), 8.70 (1H, t, J = 8.0
Hz). 6-1374 .delta. 7.41-7.49 (2H, m), 8.00 (1H, t, J = 8.0 Hz),
8.11 (2H, s), 8.16 (1H, s), 8.34 (1H, d, J = 7.2 Hz), 8.58 (1H, d,
J = 2.0 Hz), 8.70 (1H, t, J = 7.8 Hz), 8.78 (1H, s). 6-1381 .delta.
7.43 (1H, t, J = 8.0 Hz), 7.53 (1H, d, J = 8.0 Hz), 7.97 (1H, t, J
= 7.8 Hz), 8.11-8.12 (3H, m), 8.14 (1H, s), 8.22 (1H, d, J = 8.0
Hz), 8.57 (1H, t, J = 8.0 Hz), 8.94 (1H, s). 6-1574 .delta.
7.37-7.41 (1H, m), 7.53-7.64 (3H, m), 7.86-7.94 (4H, m), 8.13-8.22
(3H, m), 8.67-8.72 (1H, m). 6-1575 .delta. 7.22-7.27 (1H, m),
7.35-7.41 (2H, m), 7.57-7.60 (1H, m), 7.88-7.93 (2H, m), 8.16 (1H,
s), 8.20-8.25 (2H, m), 8.74-8.75 (1H, m), 8.77-9.00 (1H, m). 6-1576
.delta. 7.27-7.37 (2H, m), 7.48-7.53 (1H, m), 7.72-7.80 (3H, m),
7.92 (1H, s), 8.15 (1H, s), 8.27-8.31 (1H, m), 9.16 (1H, s), 9.35
(1H, d, J = 7.3 Hz). 6-1577 .delta. 7.20-7.23 (3H, m), 7.24-7.26
(1H, m), 7.39-7.40 (3H, m), 7.86-7.97 (1H, m), 8.06 (1H, d, J = 2.4
Hz), 8.16-8.20 (1H, m), 8.62-8.67 (1H, m). 6-1594 .delta. 7.41-7.42
(1H, m), 7.70-7.71 (1H, m), 7.93-8.89 (3H, m), 8.12-8.24 (5H, m),
8.60-8.61 (1H, m). 6-1595 .delta. 7.41 (1H, t, J = 7.8 Hz),
7.84-7.87 (2H, m), 7.90-7.94 (2H, m), 8.03-8.05 (2H, m), 8.12-8.18
(3H, m), 8.62-8.66 (1H, m). 6-1596 .delta. 7.00-7.09 (2H, m),
7.40-7.41 (1H, m), 7.46-7.53 (1H, m), 7.89-7.92 (2H, m), 8.00 (1H,
s), 8.16-8.19 (2H, m), 8.71-8.72 (1H, m). 6-1610 .delta. 7.42-7.49
(2H, m), 7.93-7.94 (2H, m), 8.15-8.21 (2H, m), 8.31-8.34 (1H, m),
8.57-8.59 (1H, m), 8.63-8.69 (2H, m). 6-1617 .delta. 7.31-7.38 (1H,
m), 7.49 (1H, d, J = 8.3 Hz), 7.82-7.86 (1H, m), 7.92 (1H, s), 8.15
(1H, s), 8.19-8.23 (1H, m), 8.30 (1H, dd, J = 2.4, 8.3 Hz),
9.04-9.09 (2H, m), 9.53 (1H, s). 6-1652 .delta. 7.40 (1H, t, J =
7.8 Hz), 7.53-7.64 (3H, m), 7.86-7.94 (4H, m), 8.13-8.20 (3H, m),
8.71-8.72 (1H, m). 6-1653 .delta. 7.22-7.25 (1H, m), 7.35-7.41 (2H,
m), 7.57-7.60 (1H, m), 7.88-7.92 (2H, m), 8.15 (1H, s), 8.20-8.29
(2H, m), 8.71-8.75 (1H, m), 8.89-8.93 (1H, m). 6-1654 .delta.
7.32-7.34 (1H, m), 7.38-7.42 (1H, m), 7.50-7.56 (1H, m), 7.63-7.70
(2H, m), 7.88-7.91 (2H, m), 8.09-8.20 (3H, m), 8.63-8.68 (1H, m).
6-1655 .delta. 7.21-7.30 (2H, m), 7.37-7.41 (1H, m), 7.86-7.97 (4H,
m), 8.06-8.21 (3H, m), 8.63-8.67 (1H, m). 6-1672 .delta. 7.37-7.41
(1H, m), 7.67-7.71 (1H, m), 7.88-7.91 (3H, m), 8.15-8.18 (2H, m),
8.24-8.28 (3H, m), 8.52-8.56 (1H, m). 6-1673 .delta. 7.39-7.44 (1H,
m), 7.85-7.93 (4H, m), 8.03-8.05 (2H, m), 8.13-8.18 (3H, m),
8.61-8.65 (1H, m). 6-1674 .delta. 7.04-7.09 (2H, m), 7.38-7.42 (1H,
m), 7.47-7.52 (1H, m), 7.89-7.93 (2H, m), 8.00 (1H, s), 8.14-8.20
(2H, m), 8.69-8.73 (1H, m). 6-1688 .delta. 7.42 (1H, t, J = 7.8
Hz), 7.47 (1H, dd, J = 4.9, 7.8 Hz), 7.92-7.96 (2H, m), 8.14 (1H,
s), 8.19 (1H, d, J = 12.7 Hz), 8.33 (1H, dd, J = 2.0, 7.8 Hz), 8.58
(1H, dd, J = 2.0, 4.9 Hz), 8.70-8.71 (1H, m), 8.74 (1H, s). 6-1695
.delta. 7.39-7.43 (1H, m), 7.52-7.54 (1H, m), 7.92-7.95 (2H, m),
8.08-8.09 (1H, m), 8.15 (1H, s), 8.17-8.23 (2H, m), 8.57-8.93 (1H,
m), 8.94 (1H, s). 6-1730 .delta. 7.40 (1H, t, J = 7.8 Hz),
7.53-7.64 (3H, m), 7.87-7.95 (4H, m), 8.14 (1H, s), 8.22 (1H, d, J
= 12.7 Hz), 8.37 (1H, s), 8.71-8.72 (1H, m). 6-1731 .delta.
7.22-7.25 (1H, m), 7.35-7.37 (2H, m), 7.58-7.60 (1H, m), 7.90 (1H,
t, J = 8.6 Hz), 7.96 (1H, s), 8.22 (1H, t, J = 8.8 Hz), 8.29-8.32
(1H, d, J = 12.4 Hz), 8.37 (1H, s), 8.73 (1H, m), 8.94 (1H, s).
6-1732 .delta. 7.32-7.33 (1H, m), 7.37 (1H, t, J = 8.0 Hz),
7.52-7.54 (1H, m), 7.64-7.70 (2H, m), 7.90 (1H, t, J = 6.4 Hz),
7.96 (1H, s), 8.10 (1H, s), 8.23 (1H, d, J = 12.0 Hz), 8.37 (1H,
s), 8.65 (1H, t, J = 8.0 Hz). 6-1733 .delta. 7.19-7.25 (2H, m),
7.35 (1H, t, J = 7.8 Hz), 7.87-7.97 (4H, m), 8.08 (1H, s), 8.25
(1H, d, J = 12.0 Hz), 8.37 (1H, s), 8.65 (1H, t, J = 8.0 Hz).
6-1734 .delta. 7.43-7.52 (5H, m), 7.87-7.95 (3H, m), 8.22 (1H, d, J
= 10.0 Hz), 8.35 (1H, d, J = 8.2 Hz), 8.74 (1H, t, J = 8.4 Hz).
6-1750 .delta. 7.40 (1H, t, J = 8.2 Hz), 7.68 (1H, t, J = 8.0 Hz),
7.88-7.95 (2H, m), 8.12 (1H, s), 8.16 (1H, d, J = 8.0 Hz),
8.23-8.25 (2H, m), 8.30-8.33 (1H, m), 8.36 (1H, s), 8.53 (1H, t, J
= 7.4 Hz). 6-1751 .delta. 7.44 (1H, t, J = 8.0 Hz), 7.86 (2H, d, J
= 8.0 Hz), 7.91-7.96 (2H, m), 8.03 (2H, d, J = 7.6 Hz), 8.13-8.22
(2H, m), 8.37 (1H, s), 8.64 (1H, t, J = 8.6 Hz). 6-1752 .delta.
7.04-7.11 (2H, m), 7.38-7.53 (2H, m), 7.90-7.95 (2H, m), 8.01 (1H,
s), 8.22 (1H, d, J = 12.8 Hz), 8.37 (1H, s), 8.69-8.73 (1H, m).
6-1754 .delta. 7.39-7.44 (2H, m), 7.54 (1H, s), 7.85 (1H, d, J =
8.0 Hz), 7.90-7.95 (2H, m), 8.22 (1H, d, J = 12.0 Hz), 8.68 (1H,
s), 8.70 (1H, s), 8.69 (1H, t, J = 7.8 Hz). 6-1755 .delta.
7.16-7.19 (1H, m), 7.40 (1H, t, J = 8.0 Hz), 7.92-7.95 (2H, m),
8.07 (2H, t, J = 4.8 Hz), 8.24 (1H, d, J = 12.8 Hz), 8.37 (1H, s),
8.42 (1H, s), 8.70 (1H, t, J = 8.0 Hz). 6-1766 .delta. 7.41-7.49
(2H, m), 7.93-7.97 (2H, m), 8.22 (1H, d, J = 13.2 Hz), 8.33 (1H,
dd, J = 2.0, 7.3 Hz), 8.37 (1H, s), 8.58 (1H, dd, J = 2.0, 4.9 Hz),
8.70-8.73 (2H, m). 6-1773 .delta. 7.40 (1H, t, J = 8.2 Hz), 7.52
(1H, d, J = 8.0 Hz), 7.91-7.96 (2H, m), 8.12-8.28 (3H, m), 8.37
(1H, s), 8.57 (1H, s), 8.94 (1H, s). 6-1808 .delta. 7.38-7.42 (1H,
m), 7.53-7.64 (3H, m), 7.87-7.94 (4H, m), 8.14 (1H, s), 8.23-8.26
(1H, m), 8.36 (1H, s), 8.68-8.71 (1H, m). 6-1809 .delta. 7.22-7.25
(2H, m), 7.38 (1H, t, J = 8.0 Hz), 7.58-7.61 (1H, m), 7.89-7.94
(2H, m), 8.23 (1H, t, J = 6.3 Hz), 8.29 (1H, d, J = 13.2 Hz), 8.36
(1H, s), 8.74 (1H, t, J = 6.3 Hz), 8.93-8.94 (1H, m). 6-1810
.delta. 7.30-7.33 (2H, m), 7.40 (1H, t, J = 7.8 Hz), 7.51-7.56 (1H,
m), 7.64-7.70 (2H, m), 7.88-7.94 (1H, m), 8.10 (1H, s), 8.23 (1H,
d, J = 12.2 Hz), 8.36 (1H, s), 8.67 (1H, t, J = 7.8 Hz). 6-1811
.delta. 7.39 (1H, t, J = 8.3 Hz), 7.86-7.97 (3H, m), 8.08 (2H, s),
8.25 (1H, d, J = 12.2 Hz), 8.36 (2H, s), 8.65 (2H, t, J = 6.3 Hz).
6-1828 .delta. 7.30-7.33 (2H, m), 7.41 (1H, t, J = 7.6 Hz),
7.68-7.73 (1H, m), 7.89-7.94 (2H, m), 8.16 (1H, d, J = 7.6 Hz),
8.23-8.27 (1H, m), 8.41 (1H, s), 8.63-8.64 (2H, m). 6-1829 .delta.
7.29-7.31 (1H, m), 7.42 (1H, t, J = 8.0 Hz), 7.90-7.94 (2H, m),
8.04 (2H, d, J = 4.4 Hz), 8.15 (1H, s), 8.23 (1H, d, J = 12.0 Hz),
8.36 (1H, s), 8.60-8.66 (2H, m). 6-1830 .delta. 7.06 (1H, t, J =
8.3 Hz), 7.41 (1H, t, J = 7.8 Hz), 7.67-7.69 (1H, m), 7.90-7.93
(2H, m), 8.03 (1H, s), 8.25 (1H, d, J = 12.7 Hz), 8.35 (1H, s),
8.61 (1H, s), 8.70 (1H, t, J = 7.8 Hz). 6-1851 .delta. 7.42 (1H, t,
J = 8.0 Hz), 7.53 (1H, d, J = 7.9 Hz), 7.92-7.94 (2H, m), 8.09 (1H,
s), 8.21-8.24 (2H, m), 8.36 (1H, s), 8.59 (1H, t, J = 8.0 Hz), 8.94
(1H, s). 6-2110 .delta. 7.36-7.40 (1H, m), 7.53-7.64 (3H, m),
7.84-7.97 (1H, m), 7.92-7.94 (2H, m), 8.04-8.07 (1H, m), 8.08-8.13
(1H, m), 8.20 (2H, s), 8.68-8.72 (1H, m). 6-3348 .delta. 7.29-7.34
(1H, m), 7.53-7.65 (3H, m), 7.80-7.84 (1H, m), 7.90-7.92 (3H, m),
8.14 (1H, broad-s), 8.20 (1H, d, J = 2.9 Hz), 8.25 (1H, broad-s),
9.10 (1H, dd, J = 1.9, 7.3 Hz). 6-3384 .delta. 7.32-7.36 (1H, m),
7.45-7.48 (1H, m), 7.83-7.87 (1H, m), 7.93 (1H, broad-s), 8.10 (1H,
broad-s), 8.15 (1H, broad-s), 8.30 (1H, dd, J = 1.5, 7.3 Hz),
8.57-8.79 (1H, m), 8.78 (1H, broad-s), 9.09 (1H, dd, J = 2.4, 7.3
Hz). 6-5902 (DMSO-d.sub.6) .delta. 7.39 (1H, t, J = 7.8 Hz),
7.52-7.64 (4H, m), 7.81 (1H, t, J = 6.8 Hz), 7.95 (1H, s),
7.98-8.01 (3H, m), 10.29 (1H, s), 10.68 (1H, s). 6-5903 .delta.
7.50-7.67 (5H, m), 7.79 (1H, d, J = 8.0 Hz), 7.92 (1H, d, J = 8.0
Hz), 8.01 (2H, d, J = 8.0 Hz), 8.10 (2H, s), 8.31 (1H, s). 6-5904
.delta. 7.19-7.23 (1H, m), 7.28-7.31 (1H, m), 7.58 (1H, t, J = 8.2
Hz), 7.78 (1H, d, J = 8.0 Hz), 7.91-7.94 (3H, m), 8.01 (2H, d, J =
8.0 Hz), 8.30 (2H, s), 8.61 (1H, s). 6-5905 .delta. 7.26 (1H, s),
7.43-7.46 (1H, m), 7.56-7.60 (1H, m), 7.80-7.94 (5H, m), 8.22-8.56
(4H, m). 6-5906 .delta. 7.18-7.12 (2H, m), 7.53-7.57 (1H, m), 7.76
(1H, d, J = 7.6 Hz), 7.86-8.28 (7H, m), 8.28 (1H, s). 6-5907
.delta. 7.39 (1H, t, J = 7.8 Hz), 7.52-7.64 (4H, m), 7.85-7.94 (4H,
m), 8.06 (1H, d, J = 12.2 Hz), 8.14 (1H, broad-s), 8.67-8.71 (1H,
m). 6-5908 .delta. 7.39-7.49 (2H, m), 7.59 (1H, s), 7.88-7.94 (2H,
m), 8.07 (1H, d, J = 12.2 Hz), 8.31-8.33 (1H, m), 8.57-8.58 (1H,
m), 8.60-8.70 (1H, m), 8.74 (1H, broad-s). 6-5909 .delta. 7.42 (1H,
t, J = 7.8 Hz), 7.59 (1H, s), 7.85-7.92 (4H, m), 7.99 (1H,
broad-s), 8.02-8.05 (2H, m), 8.10 (1H, broad-s), 8.61-8.67 (1H, m).
6-5910 .delta. 7.39 (1H, t, J = 8.3 Hz), 7.53-7.64 (3H, m),
7.88-7.94 (4H, m), 8.13 (1H, broad-s), 8.19 (1H, broad-s), 8.24
(1H, d, J = 13.2 Hz), 8.70-8.72 (1H, m). 6-5911 .delta. 7.41 (1H,
t, J = 8.3 Hz), 7.84-7.87 (3H, m), 7.91-7.95 (1H, m), 8.03-8.05
(2H, m), 8.10 (1H, broad-s), 8.17-8.20 (2H, m), 8.63-8.67 (1H, m).
6-5912 .delta. 3.10 (3H, s), 7.59 (1H, t, J = 7.8 Hz), 7.76 (1H, d,
J = 7.8 hz), 7.77-8.00 (5H, m), 8.03 (1H, s), 8.19 (1H, s), 8.24
(1H, s), 8.36 (1H, s). 6-5913 .delta. 7.51-7.62 (4H, m), 7.72 (1H,
dd, J = 1.5, 7.8 Hz), 7.89-8.00 (6H, m), 8.14 (1H, s), 8.27 (1H, t,
J = 2.0 Hz). 6-5914 .delta. 7.44 (1H, dd, J = 4.9, 7.8 Hz),
7.56-7.60 (1H, m), 7.76 (1H, d, J = 7.8 Hz), 7.92 (3H, broad-s),
8.14 (1H, s), 8.22-8.27 (1H, m), 8.27 (1H, s), 8.41 (1H, s), 8.55
(1H, dd, J = 2.0, 4.4 Hz). 7-38 .delta. 3.57 (3H, s), 7.21-7.24
(1H, m), 7.32-7.34 (4H, m), 7.40-7.44 (2H, m), 7.59 (1H, s), 7.71
(1H, d, J = 8.0 Hz), 7.84 (3H, s). 7-39 .delta. 3.54 (3H, s),
7.06-7.19 (1H, m), 7.28-7.34 (2H, m), 7.43-7.48 (2H, m), 7.57 (1H,
s), 7.69 (1H, s), 7.75 (1H, d, J = 8.0 Hz), 7.90 (1H, d, J = 8.0
Hz), 8.06 (2H, s). 7-45 .delta. 3.57 (3H, s), 7.29-7.30 (2H, m),
7.48 (1H, t, J = 8.0 Hz), 7.59 (1H, s), 7.68-7.71 (3H, m), 7.77
(1H, d, J = 7.8 Hz), 7.85 (2H, s), 8.24 (1H, s). 7-46 .delta. 3.57
(3H, s), 7.41-7.45 (3H, m), 7.52 (2H, s), 7.55 (1H, d, J = 8.0 Hz),
7.69 (1H, s), 7.74 (1H, d, J = 7.8 Hz), 7.86 (2H, s), 8.62 (1H, s).
7-47 .delta. 3.56 (3H, s), 6.97-7.05 (3H, m), 7.17-7.19 (1H, m),
7.43-7.50
(3H, m), 7.73 (1H, s), 7.85 (2H, s). 7-57 .delta. 3.57 (3H, s),
7.15 (1H, t, J = 6.0 Hz), 7.41 (2H, s), 7.50 (1H, s), 7.52 (1H, s),
7.60 (1H, d, J = 6.4 Hz), 7.73 (1H, s), 7.85 (2H, s), 8.27 (1H, s).
7-60 3.57 (3H, s), 7.30 (1H, d, J = 8.0 Hz), 7.47 (1H, t, J = 8.0
Hz), 7.61 (1H, s), 7.76 (2H, s), 7.78-7.81 (1H, m), 7.85 (2H, s),
8.11 (1H, s), 8.24 (1H, s). 7-71 .delta. 3.56 (3H, s), 7.20-7.25
(1H, m), 7.33-7.38 (3H, m), 7.43-7.47 (3H, m), 7.56 (1H, s), 7.74
(1H, d, J = 6.8 Hz), 8.06-8.10 (3H, m). 7-72 .delta. 3.55 (3H, s),
7.06-7.10 (1H, m), 7.30-7.36 (2H, m), 7.43-7.48 (2H, m), 7.57 (1H,
s), 7.68 (1H, s), 7.78 (1H, d, J = 8.0 Hz), 7.90 (1H, d, J = 8.0
Hz), 8.07 (2H, s). 7-78 .delta. 3.57 (3H, s), 7.29-7.64 (2H, m),
7.70 (1H, s), 7.79 (1H, d, J = 8.0 Hz), 7.86 (1H, d, J = 8.0 Hz),
7.95 (1H, t, J = 8.0 Hz), 8.08 (2H, s), 8.33 (1H, d, J = 8.0 Hz),
8.40 (1H, s), 8.71 (1H, s). 7-79 .delta. 3.58 (3H, s), 7.42-7.53
(3H, m), 7.60-7.66 (1H, m), 7.77 (1H, d, J = 8.0 Hz), 7.89 (1H, t,
J = 8.0 Hz), 8.08 (2H, s), 8.21 (1H, d, J = 8.0 Hz), 8.70 (2H, s).
7-80 .delta. 3.56 (3H, s), 7.02 (1H, t, J = 8.0 Hz), 7.42-7.44 (1H,
m), 7.55 (1H, t, J = 8.0 Hz), 7.75 (1H, d, J = 8.0 Hz), 7.90-7.95
(3H, m), 8.01 (1H, s), 8.14 (1H, s), 8.26 (1H, s). 7-90 .delta.
3.59 (3H, s), 7.59 (1H, s), 7.60 (1H, d, J = 6.0 Hz), 7.80-7.83
(1H, m), 8.08 (2H, s), 8.26-8.30 (2H, m), 8.53 (1H, d, J = 4.0 Hz),
8.69 (2H, s). 7-93 .delta. 3.58 (3H, s), 7.34-7.52 (3H, m), 7.63
(1H, d, J = 16.0 Hz), 7.69 (1H, d, J = 8.0 Hz), 7.80 (1H, d, J =
8.0 Hz), 7.85 (1H, t, J = 8.0 Hz), 8.25 (1H, s), 8.29 (1H, d, J =
8.0 Hz), 8.69 (1H, s). 7-132 .delta. 3.57 (3H, s), 7.26-7.28 (1H,
m), 7.41-7.46 (3H, m), 7.52-7.54 (3H, m), 7.63 (1H, s), 7.68 (1H,
d, J = 7.8 Hz), 7.87 (1H, s), 7.98 (1H, s). 7-147 .delta. 3.58 (3H,
s), 7.14 (1H, dd, J = 4.9, 7.8 Hz), 7.41-7.42 (2H, m), 7.52 (1H,
s), 7.59 (1H, dd, J = 1.5, 7.8 Hz), 7.67 (2H, broad-s), 7.87 (1H,
s), 7.97 (1H, s), 8.26 (1H, dd, J = 1.5, 4.9 Hz). 7-268 .delta.
3.49 (3H, s), 7.12-7.16 (2H, m), 7.21-7.28 (4H, m), 7.35 (1H, t, J
= 7.8 Hz), 7.64 (1H, s), 7.70 (1H, dd, J = 1.5, 8.8 Hz), 7.86 (1H,
s), 8.07 (1H, d, J = 1.5 Hz), 8.29 (1H, s). 7-269 .delta. 3.54 (3H,
s), 6.80-6.81 (1H, m), 7.70-7.08 (1H, m), 7.25-7.26 (1H, m),
7.39-7.41 (4H, m), 7.52-7.53 (1H, m), 7.70-7.71 (1H, m), 7.90 (1H,
s), 8.12 (1H, s). 7-270 .delta. 3.55 (3H, s), 6.97-6.99 (1H, m),
7.04-7.06 (2H, m), 7.15-7.21 (1H, m), 7.32-7.34 (1H, m), 7.44 (1H,
t, J = 7.8 Hz), 7.58-7.59 (2H, m), 7.70 (1H, d, J = 7.8 Hz), 7.90
(1H, s), 8.12 (1H, s). 7-271 .delta. 3.55 (3H, s), 6.88-6.92 (2H,
m), 7.30-7.34 (3H, m), 7.43 (1H, t, J = 7.8 Hz), 7.57-7.58 (2H, m),
7.67-7.69 (1H, m), 7.90-7.91 (1H, m), 8.13-8.14 (1H, m). 7-285
.delta. 3.59 (3H, s), 7.34-7.52 (3H, m), 7.65-7.73 (4H, m), 7.90
(1H, s), 8.13-8.16 (3H, m). 7-286 .delta. 3.59 (3H, s), 7.29-7.30
(1H, m), 7.42-7.52 (4H, m), 7.63 (1H, s), 7.69 (1H, d, J = 7.8 Hz),
7.91 (1H, s), 8.08-8.13 (3H, m). 7-288 .delta. 3.57 (3H, s),
7.15-7.37 (2H, m), 7.47-7.48 (1H, m), 7.52-7.62 (5H, m), 7.72 (1H,
d, J = 7.8 Hz), 7.91 (1H, s), 8.14 (1H, s). 7-289 .delta. 3.57 (3H,
s), 7.26-7.29 (1H, m), 7.40-7.46 (3H, m), 7.52 (2H, d, J = 8.3 Hz),
7.58-7.61 (2H, m), 7.70 (1H, d, J = 7.8 Hz), 7.92 (1H, s), 8.14
(1H, s). 7-290 .delta. 3.55 (3H, s), 6.70-6.74 (2H, m), 7.14-7.19
(1H, m), 7.43-7.44 (2H, m), 7.52 (1H, s), 7.67 (1H, s), 7.74-7.77
(1H, m), 7.91 (1H, s), 8.13 (1H, s). 7-299 .delta. 3.58 (3H, s),
7.33 (1H, d, J = 6.8 Hz), 7.52 (1H, t, J = 7.8 Hz), 7.64-7.65 (2H,
m), 7.75-7.79 (3H, m), 7.83 (1H, s), 7.92 (1H, s), 8.14 (1H, s).
7-300 .delta. 3.56 (3H, broad-s), 7.14 (1H, broad-d, J = 8.3 Hz),
7.33-7.53 (4H, m), 7.59-7.60 (2H, m), 7.71-7.72 (1H, m), 7.92 (1H,
s), 8.14 (1H, s). 7-301 .delta. 3.57 (3H, s), 7.33-7.59 (4H, m),
7.60 (1H, s), 7.64 (1H, s), 7.68-7.70 (2H, m), 7.92 (1H, s), 8.15
(1H, s). 7-303 .delta. 3.56 (3H, s), 7.17-7.12 (1H, m), 7.39-7.45
(2H, m), 7.55 (2H, s), 7.69 (1H, d, J = 7.8 Hz), 7.90 (2H, s),
8.13-8.14 (2H, m). 7-304 .delta. 3.54 (3H, s), 7.10 (1H, dd, J =
4.9, 7.8 Hz), 7.35-7.40 (2H, m), 7.56 (1H, dd, J = 1.5, 7.8 Hz),
7.70 (2H, s), 7.88-7.90 (2H, m), 8.12 (1H, s), 8.22 (1H, dd, J =
1.5, 4.9 Hz). 7-305 .delta. 3.57 (3H, s), 7.13 (1H, dd, J = 4.9,
7.8 Hz), 7.41-7.42 (2H, m), 7.57-7.62 (2H, m), 7.67-7.69 (2H, m),
7.91 (1H, s), 8.13 (1H, s), 8.24-8.26 (1H, m). 7-311 .delta. 3.57
(3H, s), 7.23-7.31 (2H, m), 7.47-7.48 (1H, m), 7.66-7.73 (4H, m),
7.92 (1H, s), 8.14 (1H, s), 8.23 (1H, d, J = 1.9 Hz). 7-316 .delta.
3.59 (3H, s), 7.27-7.30 (1H, m), 7.48-7.49 (1H, m), 7.60-7.67 (3H,
m), 7.73 (1H, d, J = 7.8 Hz), 7.85 (1H, dd, J = 1.9, 7.8 Hz), 7.92
(1H, s), 8.15 (1H, d, J = 1.5 Hz), 8.52 (1H, s). 7-346 .delta. 3.54
(3H, s), 7.18-7.34 (4H, m), 7.40 (1H, t, J = 7.8 Hz), 7.57 (1H, s),
7.67-7.69 (1H, m), 7.88 (1H, s), 8.10 (1H, s). 7-347 .delta. 3.53
(3H, s), 6.82 (1H, s), 7.07 (1H, s), 7.23-7.70 (7H, m), 7.89 (1H,
s), 8.11 (1H, s). 7-348 .delta. 3.53 (3H, s), 6.96-6.99 (1H, m),
7.00-7.06 (2H, m), 7.15-7.19 (1H, m), 7.32-7.34 (1H, m), 7.42-7.46
(1H, m), 7.60 (1H, s), 7.68-7.71 (2H, m), 7.89 (1H, s), 8.11 (1H,
s). 7-349 .delta. 3.54 (3H, s), 6.88-6.92 (2H, m), 7.29-7.34 (3H,
m), 7.41-7.44 (2H, m), 7.59 (1H, s), 7.68-7.70 (1H, m), 7.89 (1H,
s), 8.11 (1H, s). 7-366 .delta. 3.64 (3H, s), 7.31-7.36 (2H, m),
7.44-7.48 (2H, m), 7.52-7.58 (1H, m), 7.61 (2H, s), 7.71-7.73 (2H,
m), 7.89 (1H, s), 8.12 (1H, s). 7-367 .delta. 3.56 (3H, s),
7.22-7.31 (3H, m), 7.44-7.48 (1H, m), 7.66-7.77 (4H, m), 7.90 (1H,
s), 8.12 (1H, s), 8.22 (1H, s). 7-368 .delta. 3.52 (3H, s),
6.67-6.72 (2H, m), 7.00 (1H, s), 7.13-7.17 (1H, m), 7.41-7.42 (2H,
m), 7.72-7.89 (3H, m), 8.11 (1H, s). 7-382 .delta. 3.58 (3H, s),
7.13-7.16 (1H, m), 7.43-7.61 (4H, m), 7.67 (2H, s), 7.90 (1H, s),
8.13 (1H, s), 8.26-8.27 (1H, m). 7-389 .delta. 3.57 (3H, s), 7.29
(1H, s), 7.40-7.46 (3H, m), 7.52-7.54 (2H, m), 7.59-7.62 (1H, m),
7.69-7.70 (1H, m), 7.90 (1H, s), 8.13 (1H, s). 7-424 .delta. 3.56
(3H, s), 7.19-7.37 (6H, m), 7.44-7.45 (1H, m), 7.54 (1H, s), 7.60
(1H, broad-s), 7.68 (1H, d, J = 7.8 Hz), 7.92 (1H, s), 8.31 (1H,
s). 7-425 .delta. 3.54 (3H, broad-s), 6.82 (1H, broad-s), 7.07 (1H,
broad-s), 7.23-7.30 (2H, m), 7.31-7.51 (3H, m), 7.52-7.56 (1H, m),
7.71 (1H, broad-s), 7.92 (1H, s), 8.33 (1H, s). 7-426 .delta. 3.56
(3H, s), 6.96-7.00 (1H, m), 7.05-7.07 (2H, m), 7.15-7.21 (1H, m),
7.34-7.36 (1H, m), 7.46-7.47 (1H, m), 7.58-7.66 (2H, m), 7.71 (1H,
d, J = 7.3 Hz), 7.93 (1H, s), 8.33 (1H, s). 7-427 .delta. 3.56 (3H,
s), 6.88-6.92 (2H, m), 7.31-7.34 (2H, m), 7.45-7.46 (1H, m), 7.56
(1H, s), 7.62 (1H, s), 7.65 (1H, s), 7.70 (1H, d, J = 7.3 Hz), 7.93
(1H, s), 8.33 (1H, s). 7-428 .delta. 3.58 (3H, s), 7.00-7.24 (4H,
m), 7.42-7.43 (3H, m), 7.62 (1H, s), 7.66 (1H, s), 7.94 (1H, s),
8.34 (1H, s). 7-444 .delta. 3.57 (3H, s), 7.33-7.37 (2H, m),
7.48-7.49 (1H, m), 7.52-7.61 (4H, m), 7.69-7.74 (2H, m), 7.93 (1H,
s), 8.34 (1H, s). 7-445 .delta. 3.58 (3H, s), 7.30 (1H, d, J = 9.5
Hz), 7.41-7.48 (3H, m), 7.51-7.53 (3H, m), 7.59 (1H, s), 7.70 (1H,
d, J = 7.9 Hz), 7.94 (1H, s), 8.34 (1H, s). 7-446 .delta. 3.56 (3H,
s), 6.69-6.73 (2H, m), 7.14-7.18 (1H, m), 7.44-7.45 (2H, m), 7.61
(1H, s), 7.69 (1H, s), 7.75-7.77 (1H, m), 7.93 (1H, s), 8.34 (1H,
s). 7-449 .delta. 3.51 (3H, s), 6.82-6.86 (1H, m), 6.94-6.98 (1H,
m), 7.14-7.24 (1H, m), 7.28-7.29 (2H, m), 7.41 (1H, s), 7.64 (1H,
s), 7.69 (1H, d, J = 5.9 Hz), 7.94 (1H, s), 8.34 (1H, s). 7-460
.delta. 3.59 (3H, s), 7.13 (1H, dd, J = 4.8, 7.1 Hz), 7.43-7.44
(2H, m), 7.52 (1H, s), 7.58-7.60 (1H, m), 7.67 (2H, broad-s), 7.94
(1H, s), 8.26 (1H, dd, J = 1.6, 4.8 Hz), 8.34 (1H, s). 7-467
.delta. 3.58 (3H, s), 7.23 (1H, d, J = 8.3 Hz), 7.33 (1H, d, J =
7.8 Hz), 7.49-7.50 (1H, m), 7.62 (1H, s), 7.67-7.68 (2H, m), 7.73
(1H, d, J = 7.8 Hz), 7.93 (1H, s), 8.23 (1H, d, J = 2.0 Hz), 8.34
(1H, s). 7-502 .delta. 3.57 (3H, s), 7.20-7.26 (3H, m), 7.27-7.37
(3H, m), 7.45 (1H, t, J = 7.6 Hz), 7.56 (1H, s), 7.68 (1H, s), 7.71
(1H, d, J = 8.0 Hz), 7.91 (1H, s), 8.31 (1H, s). 7-504 3.56 (3H,
s), 6.96-7.01 (1H, m), 7.06 (2H, d, J = 7.2 Hz), 7.18 (1H, t, J =
6.8 Hz), 7.35 (1H, d, J = 8.0 Hz), 7.45 (1H, t, J = 8.0 Hz), 7.56
(2H, s), 7.71 (1H, d, J = 8.0 Hz), 7.91 (1H, s), 8.32 (1H, s).
7-505 .delta. 3.57 (3H, s), 6.90 (2H, t, J = 8.8 Hz), 7.31-7.35
(3H, m), 7.45 (1H, t, J = 8.0 Hz), 7.54 (2H, d, J = 13.6 Hz), 7.69
(1H, d, J = 8.0 Hz), 7.91 (1H, s), 8.32 (1H, s). 7-522 .delta. 3.57
(3H, s), 7.32-7.37 (2H, m), 7.46 (1H, t, J = 8.0 Hz), 7.55 (1H, t,
J = 7.6 Hz), 7.59 (2H, d, J = 8.0 Hz), 7.75 (1H, d, J = 8.0 Hz),
7.88 (1H, s), 7.92 (2H, s), 8.33 (1H, s). 7-523 .delta. 3.56 (3H,
s), 7.41-7.47 (4H, m), 7.53 (2H, d, J = 8.2 Hz), 7.61 (1H, s),
7.71-7.72 (2H, m), 7.92 (1H, s), 8.33 (1H, s). 7-538 .delta. 3.58
(3H, s), 7.14 (1H, t, J = 6.0 Hz), 7.40-7.43 (2H, m), 7.56-7.58
(2H, m), 7.68-7.69 (2H, m), 7.92 (1H, s), 8.26 (1H, s), 8.33 (1H,
s). 7-804 .delta. 3.55 (3H, s), 7.19-7.52 (9H, m), 7.62 (1H, d, J =
7.8 Hz), 8.16 (2H, s). 7-824 .delta. 3.57 (3H, s), 7.33-7.75 (7H,
m), 7.98-7.99 (1H, m), 8.12 (2H, s), 8.18-8.43 (1H, m). 7-825
.delta. 3.57 (3H, s), 7.22-7.66 (7H, m), 7.85-7.88 (1H, m),
7.97-7.99 (2H, m), 8.17-8.27 (1H, m). 7-840 .delta. 3.57 (3H, s),
7.13-7.26 (1H, m), 7.40-7.44 (2H, m), 7.58-7.71 (3H, m), 8.18-8.23
(4H, m). 7-948 .delta. 3.49 (3H, s), 7.23-7.52 (8H, m), 7.66 (2H,
s), 8.00 (1H, t, J = 6.8 Hz). 7-969 .delta. 3.51 (3H, s), 7.45-7.46
(3H, m), 7.53-7.55 (3H, m), 7.67 (2H, s), 7.92-7.93 (1H, m),
8.05-8.06 (1H, m). 7-984 .delta. 3.53 (3H, s), 7.13-7.16 (1H, m),
7.20-7.24 (1H, m), 7.52-7.53 (1H, m), 7.65-7.68 (3H, m), 7.99-8.03
(2H, m), 8.28-8.30 (1H, m). 7-1104 .delta. 3.51 (3H, s), 7.22-7.44
(7H, m), 7.86 (2H, s), 8.00-8.03 (2H, m). 7-1105 .delta. 3.52 (3H,
s), 6.82 (1H, t, J = 8.8 Hz), 7.06-7.08 (1H, m), 7.18-7.24 (2H, m),
7.40-7.44 (2H, m), 7.87 (3H, s), 8.01-8.05 (1H, m). 7-1106 .delta.
3.50 (3H, s), 7.00-7.23 (4H, m), 7.29-7.31 (1H, m), 7.45 (1H, s),
7.87 (3H, s), 8.03-8.07 (1H, m). 7-1107 .delta. 3.49 (3H, s),
6.91-6.93 (2H, m), 7.28-7.44 (4H, m), 7.86 (2H, s), 8.00-8.10 (2H,
m). 7-1124 .delta. 3.52 (3H, s), 7.30-7.34 (2H, m), 7.46-7.59 (3H,
m), 7.71 (1H, broad-s), 7.87 (2H, s), 7.97-8.09 (2H, m). 7-1125
.delta. 3.52 (3H, s), 7.29-7.32 (1H, m), 7.45-7.52 (5H, m), 7.84
(2H, s), 7.95-8.06 (2H, m). 7-1126 .delta. 3.49 (3H, s), 6.72-6.76
(2H, m), 7.16-7.23 (2H, m), 7.43-7.50 (1H, m), 7.88 (2H, s),
8.02-8.06 (1H, m), 8.13-8.17 (1H, m). 7-1140 .delta. 3.54 (3H, s),
7.13-7.16 (1H, m), 7.21-7.26 (1H, m), 7.43-7.46 (1H, m), 7.52 (1H,
broad-s), 7.65-7.69 (1H, m), 7.88 (2H, s), 8.00-8.04 (1H, m),
8.28-8.30 (1H, m). 7-1147 .delta. 3.52 (3H, s), 7.22-7.26 (1H, m),
7.34 (1H, t, J = 7.8 Hz), 7.46-7.52 (1H, m), 7.62-7.68 (1H, m),
7.87 (2H, s), 7.91-7.95 (1H, m), 8.07-8.11 (1H, m), 8.34 (1H,
broad-s). 7-1182 .delta. 3.51 (3H, s), 7.22-7.44 (7H, m), 7.85 (2H,
s), 8.00-8.03 (2H, m). 7-1183 .delta. 3.51 (3H, s), 6.79-6.83 (1H,
m), 7.05 (1H, t, J = 7.8 Hz), 7.17-7.23 (2H, m), 7.40-7.43 (2H, m),
7.85 (2H, s), 7.98-8.00 (2H, m). 7-1184 .delta. 3.52 (3H, s),
6.99-7.22 (4H, m), 7.28-7.30 (1H, m), 7.44-7.45 (1H, m), 7.88 (2H,
s), 8.02-8.06 (2H, m). 7-1185 .delta. 3.49 (3H, s), 6.91-7.00 (2H,
m), 7.26-7.44 (4H, m), 7.85 (2H, s), 8.01-8.10 (2H, m). 7-1202
.delta. 3.52 (3H, s), 7.26-7.32 (1H, m), 7.45-7.52 (5H, m), 7.86
(2H, s), 7.84-7.95 (1H, m), 8.06-8.08 (1H, m). 7-1203 .delta. 3.52
(3H, s), 7.26-7.32 (1H, m), 7.45-7.52 (5H, m), 7.86 (2H, s),
7.84-7.95 (1H, m), 8.06-8.08 (1H, m). 7-1204 .delta. 3.51 (3H, s),
7.02 (1H, t, J = 8.8 Hz), 7.39-7.44 (1H, m), 7.50 (1H, t, J = 7.4
Hz), 7.93 (1H, t, J = 7.8 Hz), 8.02 (1H, s), 8.10 (2H, s), 8.13
(1H, s), 8.68 (1H, t, J = 8.0 Hz). 7-1218 .delta. 3.52 (3H, s),
7.39-7.47 (1H, m), 7.96 (1H, t, J = 8.0 Hz), 8.11 (2H, s), 8.16
(1H, s), 8.33 (1H, d, J = 7.2 Hz), 8.58-8.59 (1H, m), 8.68 (1H, t,
J = 7.8 Hz), 8.78 (1H, s). 7-1225 .delta. 3.52 (3H, s), 7.22-7.24
(1H, m), 7.32-7.36 (1H, m), 7.46-7.50 (1H, m), 7.66-7.68 (1H, m),
7.85 (2H, s), 7.93-7.96 (1H, m), 8.07-8.11 (1H, m), 8.34 (1H,
broad-s). 7-1260 .delta. 4.09 (3H, s), 7.21-7.49 (7H, m), 7.99-8.08
(4H, m). 7-1261 .delta. 3.53 (3H, s), 6.79-6.83 (1H, m), 7.03-7.07
(1H, m), 7.19-7.23 (2H, m), 7.42-7.43 (2H, m), 8.01-8.10 (4H, m).
7-1262 .delta. 3.51 (3H, s), 6.99-7.00 (1H, m), 7.08-7.14 (2H, m),
7.29-7.33 (2H, m), 7.46-7.47 (1H, m), 8.05-8.12 (4H, m). 7-1263
.delta. 3.52 (3H, s), 6.88-6.93 (2H, m), 7.29-7.37 (3H, m),
7.46-7.48 (1H, m), 8.04-8.09 (4H, m). 7-1280 .delta. 3.52 (3H, s),
7.31-7.47 (2H, m), 7.49 (1H, s), 7.57 (2H, m), 7.69 (1H, s),
8.07-8.10 (4H, m). 7-1281 .delta. 3.53 (3H, s), 7.23-7.52 (6H, m),
7.90-8.09 (4H, m). 7-1282 .delta. 3.55 (3H, s), 6.72-6.76 (2H, m),
7.17-7.24 (2H, m), 7.48-7.49 (1H, m), 8.04-8.16 (4H, m). 7-1296
.delta. 3.55 (3H, s), 7.12-7.15 (1H, m), 7.46-7.51 (1H, broad-s),
7.67-7.69 (1H, m), 8.03-8.12 (5H, m), 8.27-8.29 (1H, m). 7-1303
.delta. 3.54 (3H, s), 7.20-7.23 (1H, m), 7.35-7.39 (1H, m),
7.52-7.53 (1H, m), 7.65 (1H, s), 7.97 (1H, broad-s), 8.09-8.14 (3H,
m), 8.34-8.35 (1H, m). 7-1338 .delta. 3.52 (3H, s), 7.10-7.35 (6H,
m), 7.45-7.52 (1H, m), 8.02-8.07 (4H, m). 7-1339 .delta. 3.53 (3H,
s), 6.80 (1H, t, J = 8.0 Hz), 7.04 (1H, t, J = 8.0 Hz), 7.29-7.32
(1H, m), 7.43 (1H, t, J = 8.0 Hz), 7.68-7.71 (1H, m), 8.01-8.04
(2H, m), 8.09 (2H, s), 8.63 (1H, s). 7-1340 .delta. 3.56 (3H, s),
7.04-7.08 (1H, m), 7.30-7.33 (1H, m), 7.43-7.48 (2H, m), 7.57 (1H,
s), 7.64 (1H, s), 7.77 (1H, d, J = 8.0 Hz),
7.90 (1H, d, J = 8.0 Hz), 8.07 (2H, s). 7-1341 .delta. 3.52 (3H,
s), 6.91-6.92 (2H, m), 7.30 (1H, t, J = 8.0 Hz), 7.36 (2H, s), 7.47
(1H, t, J = 8.0 Hz), 8.00-8.06 (2H, m), 8.08 (2H, s). 7-1358
.delta. 3.53 (3H, s), 7.31-7.40 (2H, m), 7.45-7.60 (3H, m), 7.69
(1H, s), 7.99-8.11 (4H, m). 7-1359 .delta. 3.53 (3H, s), 7.26-7.34
(1H, m), 7.40-7.60 (5H, m), 7.83-7.95 (1H, m), 8.01-8.06 (3H, m).
7-1360 .delta. 3.55 (3H, s), 6.72-6.76 (2H, m), 7.22-7.24 (1H, m),
7.42-7.44 (1H, m), 7.49 (1H, t, J = 8.0 Hz), 8.05 (1H, d, J = 8.0
Hz), 8.10 (2H, s), 8.17 (1H, d, J = 8.0 Hz). 7-1374 .delta. 3.55
(3H, s), 7.12-7.15 (1H, m), 7.52-7.53 (2H, m), 7.68 (1H, d, J = 8.0
Hz), 8.02-8.06 (2H, m), 8.11 (2H, s), 8.28 (1H, s). 7-1381 .delta.
3.54 (3H, s), 7.19-7.22 (1H, m), 7.37 (1H, t, J = 8.0 Hz), 7.54
(1H, t, J = 6.0 Hz), 7.66 (1H, d, J = 6.8 Hz), 7.93-7.96 (1H, m),
8.09-8.13 (3H, m), 8.35 (1H, s). 7-1417 .delta. 3.49 (3H, s),
7.23-7.26 (3H, m), 7.27-7.33 (3H, m), 7.52-7.53 (1H, m), 7.85 (1H,
s), 7.96-8.06 (3H, m). 7-1574 .delta. 3.50 (3H, s), 6.99-7.33 (6H,
m), 7.43-7.45 (1H, m), 7.90 (1H, s), 7.97-8.06 (2H, m), 8.13 (1H,
s). 7-1575 .delta. 3.52 (3H, s), 6.82-6.83 (1H, m), 7.06-7.07 (1H,
m), 7.19-7.26 (2H, m), 7.39-7.46 (2H, m), 7.91 (1H, s), 7.99-8.01
(1H, m), 8.07-8.14 (2H, m). 7-1576 .delta. 3.50 (3H, s), 7.01-7.17
(4H, m), 7.27-7.31 (1H, m), 7.46-7.52 (1H, m), 7.91 (1H, s),
8.01-8.05 (2H, m), 8.13 (1H, s). 7-1577 .delta. 3.50 (3H, s),
6.90-6.94 (2H, m), 7.26-7.35 (3H, m), 7.45-7.46 (1H, m), 7.90 (1H,
s), 8.00-8.07 (2H, m), 8.13 (1H, s). 7-1594 .delta. 3.52 (3H, s),
7.29-7.36 (2H, m), 7.50 (2H, broad-s), 7.60 (1H, broad-d, J = 6.8
Hz), 7.70 (1H, broad-s), 7.91 (1H, broad-s), 8.04-8.07 (2H, m),
8.14 (1H, s). 7-1595 .delta. 3.51 (3H, s), 7.29-7.31 (2H, m),
7.44-7.52 (4H, m), 7.92 (1H, s), 8.03-8.06 (2H, m), 8.14 (1H,
broad-s). 7-1596 .delta. 3.54 (3H, s), 6.75 (2H, broad-s),
7.17-7.26 (2H, m), 7.50-7.51 (1H, m), 7.92 (1H, s), 8.01-8.05 (1H,
m), 8.14-8.20 (2H, m). 7-1605 .delta. 3.53 (3H, s), 7.41 (1H, t, J
= 7.8 Hz), 7.53-7.55 (1H, m), 7.82-7.86 (3H, m), 7.91 (1H, s),
7.99-8.01 (1H, m), 8.10-8.14 (2H, m). 7-1606 .delta. 2.53 (3H, s),
7.15-7.17 (1H, m), 7.24-7.28 (1H, m), 7.39-7.41 (1H, m), 7.41-7.44
(1H, m), 7.53-7.56 (1H, m), 7.93 (1H, s), 8.04-8.08 (2H, m), 8.15
(1H, s). 7-1608 .delta. 3.52 (3H, s), 7.22-7.23 (1H, m), 7.29-7.33
(1H, m), 7.48-7.52 (1H, m), 7.71-7.72 (1H, m), 7.90 (1H, s),
8.00-8.03 (2H, m), 8.13 (1H, s), 8.54-8.55 (2H, m). 7-1610 .delta.
3.54 (3H, s), 7.14-7.17 (2H, m), 7.45-7.70 (2H, m), 7.96 (1H, s),
8.00-8.07 (3H, m), 8.28-8.30 (1H, m). 7-1616 .delta. 3.52 (3H, s),
7.27-7.23 (1H, m), 7.35-7.36 (1H, m), 7.49-7.51 (1H, m), 7.68 (1H,
d, J = 6.8 Hz), 7.91 (1H, s), 8.09-8.05 (2H, m), 8.13 (1H, s), 8.30
(1H, s). 7-1617 .delta. 3.52 (3H, s), 7.23-7.27 (1H, m), 7.33-7.37
(1H, m), 7.47-7.51 (1H, m), 7.67-7.68 (1H, m), 7.91 (1H, s),
8.05-8.09 (1H, m), 8.13 (2H, s), 8.30 (1H, s). 7-1638 .delta. 3.50
(3H, s), 7.19-7.27 (2H, m), 7.32-7.33 (1H, m), 7.40-7.42 (1H, m),
7.91 (1H, s), 8.00-8.02 (1H, m), 7.09-8.11 (1H, m), 8.14 (1H, s),
8.18 (1H, s), 8.56 (1H, d, J = 8.8 Hz). 7-1639 .delta. 3.52 (3H,
broad-s), 7.00-7.29 (3H, m), 7.44 (1H, broad-s), 7.52 (1H, s),
7.91-8.14 (3H, m), 8.51 (2H, broad-s). 7-1645 .delta. 3.50 (3H, s),
7.22-7.27 (2H, m), 7.33-7.37 (1H, m), 7.43-7.47 (1H, m), 7.92 (1H,
s), 8.02-8.10 (3H, m), 8.15-8.19 (2H, m). 7-1652 .delta. 3.50 (3H,
s), 7.23-7.26 (2H, m), 7.27-7.32 (4H, m), 7.44-7.45 (1H, m), 7.88
(1H, s), 7.98 (1H, t, J = 6.8 Hz), 8.04-8.08 (1H, m), 8.11 (1H, s).
7-1672 .delta. 3.51 (3H, s), 7.29-7.35 (2H, m), 7.49-7.50 (2H, m),
7.60 (1H, d, J = 6.3 Hz), 7.69 (1H, s), 7.89 (1H, s), 8.03-8.06
(2H, m), 8.12 (1H, s). 7-1673 .delta. 3.52 (3H, s), 7.29-7.32 (1H,
m), 7.44-7.52 (5H, m), 7.89 (1H, s), 8.02-8.06 (2H, m), 8.12 (1H,
s). 7-1730 .delta. 3.51 (3H, s), 7.21-7.23 (2H, m), 7.27-7.33 (4H,
m), 7.44-7.46 (1H, m), 7.92 (1H, s), 8.00 (1H, t, J = 6.3 Hz),
8.08-8.09 (1H, m), 8.33 (1H, s). 7-1731 .delta. 3.51 (3H, s),
6.79-6.83 (1H, m), 7.05 (1H, t, J = 7.6 Hz), 7.18-7.46 (4H, m),
7.94-8.00 (2H, m), 8.20 (1H, d, J = 12.4 Hz), 8.34 (1H, s). 7-1732
.delta. 3.50 (3H, s), 7.00-7.18 (4H, m), 7.27-7.31 (1H, m),
7.45-7.48 (1H, m), 7.93 (1H, s), 8.01-8.03 (1H, m), 8.12 (1H,
broad-s), 8.34 (1H, s). 7-1733 .delta. 3.50 (3H, s), 6.91 (2H, s),
6.93-7.35 (3H, m), 7.47 (1H, t, J = 7.0 Hz), 7.93 (1H, s),
8.01-8.10 (1H, m), 8.13 (1H, broad-s), 8.34 (1H, s). 7-1750 .delta.
3.52 (3H, s), 7.28-7.71 (6H, m), 7.93 (1H, s), 8.06 (1H, t, J = 8.4
Hz), 8.34 (1H, s), 8.60 (1H, s). 7-1751 .delta. 3.52 (3H, s), 7.32
(1H, t, J = 8.3 Hz), 7.44-7.52 (5H, m), 7.93 (1H, s), 8.04-8.07
(2H, m), 8.34 (1H, s). 7-1752 .delta. 3.54 (3H, s), 6.74 (2H, s),
7.16-7.24 (2H, m), 7.50 (1H, t, J = 7.4 Hz), 7.94 (1H, s),
8.01-8.05 (1H, m), 8.25 (1H, broad-s), 8.35 (1H, s). 7-1764 .delta.
3.53 (3H, s), 7.20-7.21 (1H, m), 7.32 (1H, t, J = 7.8 Hz), 7.50
(1H, t, J = 7.8 Hz), 7.70-7.71 (1H, m), 7.92 (1H, s), 8.01-8.04
(2H, m), 8.33 (1H, s), 8.53-8.54 (2H, m). 7-1766 .delta. 3.53 (3H,
s), 7.14-7.17 (1H, m), 7.23-7.25 (1H, m), 7.54-7.55 (1H, m), 7.68
(1H, d, J = 8.0 Hz), 7.95 (1H, s), 8.00 (1H, t, J = 7.0 Hz),
8.10-8.20 (1H, m), 8.28 (1H, d, J = 4.8 Hz), 8.36 (1H, s). 7-1773
.delta. 3.53 (3H, s), 7.19-7.40 (3H, m), 7.52-7.53 (1H, m),
7.67-7.68 (1H, m), 7.93 (2H, s), 8.07-8.09 (1H, m), 8.32 (1H, d, J
= 14.4 Hz), 8.35 (1H, s). 7-1794 .delta. 3.51 (3H, s), 7.18-7.23
(2H, m), 7.32 (1H, t, J = 7.8 Hz), 7.43-7.46 (1H, m), 7.92 (1H, s),
7.98-8.01 (1H, m), 8.08-8.09 (1H, m), 8.23-8.24 (1H, m), 8.32 (1H,
s), 8.56-8.59 (1H, m). 7-1808 .delta. 3.51 (3H, s), 7.23-7.43 (6H,
m), 7.44-7.60 (1H, m), 7.91 (1H, s), 7.98-8.01 (1H, m), 8.10 (1H,
broad-s), 8.32 (1H, s). 7-1809 .delta. 3.52 (3H, s), 6.80 (1H, t, J
= 8.8 Hz), 7.06 (1H, t, J = 3.6 Hz), 7.17-7.23 (2H, m), 7.39-7.44
(1H, m), 7.92-7.93 (2H, m), 7.99 (1H, t, J = 5.2 Hz), 8.16 (1H, d,
J = 13.2 Hz), 8.33 (1H, s). 7-1810 .delta. 3.48 (3H, s), 6.99-7.16
(3H, m), 7.28-7.34 (2H, m), 7.43-7.45 (1H, m), 7.72 (1H, t, J = 8.0
Hz), 7.92 (1H, s), 8.00 (1H, t, J = 8.0 Hz), 8.33 (1H, s). 7-1811
.delta. 3.53 (3H, s), 6.90 (2H, t, J = 8.0 Hz), 7.28-7.40 (3H, m),
7.46 (1H, t, J = 7.2 Hz), 7.92 (1H, s), 8.02 (1H, t, J = 8.0 Hz),
8.13 (1H, d, J = 12.4 Hz), 8.33 (1H, s). 7-1828 .delta. 3.52 (3H,
s), 7.32-7.35 (2H, m), 7.49-7.60 (3H, m), 7.69 (1H, s), 7.92 (1H,
s), 8.05-8.08 (2H, m), 8.36 (1H, s). 7-1829 .delta. 3.53 (3H, s),
7.30-7.34 (1H, m), 7.45-7.52 (5H, m), 7.92 (1H, s), 8.04-8.07 (2H,
m), 8.34 (1H, s). 7-1844 .delta. 3.54 (3H, s), 7.15 (1H, t, J = 5.2
Hz), 7.52-7.54 (1H, m), 7.68-7.71 (2H, m), 7.94 (1H, s), 8.00 (1H,
t, J = 5.2 Hz), 8.15-8.16 (1H, m), 8.28 (1H, d, J = 4.8 Hz), 8.34
(1H, s). 7-1851 .delta. 3.52 (3H, s), 7.65 (1H, d, J = 6.8 Hz),
7.92 (1H, s), 8.05-8.08 (2H, m), 8.11-8.18 (3H, m), 8.26-8.31 (1H,
m), 8.33 (1H, s). 7-3348 .delta. 3.48 (3H, s), 7.18-7.30 (6H, m),
7.45 (1H, broad-s), 7.52 (1H, broad-s), 7.74-7.76 (1H, m), 7.89
(1H, s), 8.11 (1H, s). 7-3369 .delta. 3.49 (3H, s), 7.18-7.22 (1H,
m), 7.45-7.53 (5H, m), 7.56 (2H, broad-s), 7.92 (1H, s), 8.14 (1H,
s). 7-3384 .delta. 3.52 (3H, s), 7.15-7.20 (2H, m), 7.45-7.85 (4H,
m), 7.92 (1H, s), 8.12-8.15 (1H, m), 8.27-8.29 (1H, m). 7-5902
.delta. 3.51 (3H, s), 7.00-7.52 (7H, m), 7.88 (1H, d, J = 1.5 Hz),
8.01-8.06 (3H, m). 7-5903 .delta. 3.55 (3H, s), 7.14 (1H, dd, J =
4.8, 7.8 Hz), 7.24-7.26 (1H, m), 7.40-7.60 (1H, m), 7.66-7.68 (1H,
m), 7.91 (1H, s), 8.01-8.05 (2H, m), 8.08 (1H, d, J = 1.5 Hz), 8.28
(1H, dd, J = 2.0, 4.8 Hz). 7-5904 .delta. 3.56 (3H, s), 7.05-7.09
(1H, m), 7.30-7.36 (2H, m), 7.43-7.48 (2H, m), 7.56 (1H, s), 7.65
(1H, s), 7.77 (1H, d, J = 8.0 Hz), 7.90 (1H, d, J = 8.0 Hz), 8.07
(2H, s). 7-5905 .delta. 3.57 (3H, s), 6.89 (1H, t, J = 8.0 Hz),
7.15 (1H, t, J = 8.0 Hz), 7.32-7.36 (2H, m), 7.47 (1H, t, J = 8.0
Hz), 7.53 (1H, s), 7.61 (1H, s), 7.77 (1H, d, J = 8.0 Hz), 8.09
(2H, s), 8.70 (1H, broad-s). 7-5906 .delta. 3.55 (3H, s), 7.00 (1H,
t, J = 8.0 Hz), 7.07 (2H, d, J = 7.8 Hz), 7.16-7.22 (1H, m), 7.32
(1H, d, J = 6.8 Hz), 7.44 (1H, t, J = 8.0 Hz), 7.57 (1H, s),
7.65-7.67 (1H, m), 7.74 (1H, d, J = 8.0 Hz), 7.85 (2H, s). 7-5907
.delta. 3.57 (3H, s), 6.90 (2H, t, J = 7.8 Hz), 7.29-7.34 (3H, m),
7.44 (1H, t, J = 7.8 Hz), 7.49 (1H, s), 7.62 (1H, s), 7.73 (1H, d,
J = 7.8 Hz), 7.85 (2H, s). 7-5908 .delta. 2.99 (3H, s), 3.58 (3H,
s), 7.27-7.30 (1H, m), 7.43-7.44 (1H, m), 7.51 (2H, d, J = 8.3 Hz),
7.65-7.70 (3H, m), 7.81 (2H, d, J = 8.3 Hz), 7.91 (1H, s), 8.14
(1H, s). 7-5909 .delta. 3.60 (3H, s), 7.33 (1H, d, J = 7.9 Hz),
7.50 (1H, t, J = 7.9 Hz), 7.63 (1H, s), 7.70 (1H, s), 7.75 (1H, d,
J = 7.9 Hz), 7.94 (1H, s), 8.34 (1H, s), 8.65 (2H, s), 9.10 (1H,
s). 7-5910 .delta. 3.53 (3H, s), 3.89 (3H, s), 7.32 (1H, t, J = 7.8
Hz), 7.48-7.49 (1H, m), 7.83-7.91 (2H, m), 8.01 (1H, t, J = 7.3
Hz), 8.10-8.14 (3H, m), 8.22-8.23 (1H, m). 7-5911 .delta. 3.57 (3H,
s), 7.20-7.35 (6H, m), 7.41-7.45 (2H, m), 7.53 (1H, s), 7.67 (1H,
d, J = 7.8 Hz), 7.89 (1H, s), 8.11 (1H, s). 7-5912 .delta. 3.58
(3H, s), 7.14 (1H, dd, J = 4.9, 7.8 Hz), 7.42-7.43 (2H, m), 7.55
(1H, s), 7.59 (1H, dd, J = 2.0, 7.8 Hz), 7.67-7.68 (2H, m), 7.91
(1H, s), 8.13 (1H, s), 8.26 (1H, dd, J = 2.0, 4.9 Hz). 8-268
.delta. 3.28 (2/3*3H, s), 3.39 (1/3*3H, s), 7.13-7.14 (1/3*1H, m),
7.15-7.17 (1/3*1H, m), 7.34 (1/3*1H, s), 7.36 (1/3*1H, s),
7.46-7.57 (12/3*1H, m), 7.74-7.90 (13/3*1H, m), 7.94 (2/3*1H, s),
8.05 (1/3*1H, s), 8.15 (2/3*1H, s), 8.24 (2/3*1H, s). 8-288
(CDCl.sub.3 + DMSO-d.sub.6) .delta. 3.30 (3/4*3H, s), 3.40 (1/4*3H,
s), 7.10-7.15 (1/4*1H, m), 7.20-7.25 (1/4*1H, m), 7.35 (1/4*1H, s),
7.37 (1/4*1H, s), 7.50 (3/4*1H, t, J = 7.8 Hz), 7.62-7.66 (6/4*1H,
m), 7.82-7.84 (5/4*1H, m), 7.94 (1/4*1H, s), 7.95 (3/4*1H, s), 8.00
(3/4*1H, t, J = 1.5 Hz), 8.08-8.10 (4/4*1H, m), 8.17 (3/4*1H, s),
8.18-8.19 (1/4*1H, m), 8.32-8.36 (4/4*1H, m), 8.48 (3/4*1H, t, J =
1.5 Hz), 10.00 (1/4*1H, s), 10.29 (3/4*1H, s). 8-289 .delta. 3.26
(2/3*3H, s), 3.38 (1/3*3H, s), 7.08-7.09 (1/3*1H, m), 7.12-7.14
(1/3*1H, m), 7.32 (2/3*1H, d, J = 7.8 Hz), 7.45-7.49 (3/3*1H, m),
7.72-7.76 (9/*13H, m), 7.83 (1/3*1H, s), 7.85-7.89 (4/3*1H, m),
7.95 (2/3*1H, s), 7.98-8.00 (4/3*1H, m), 8.04 (2/3*1H, d, J = 6.3
Hz), 8.16 (2/3*1H, s), 8.57 (2/3*1H, s). 8-304 .delta. 3.29
(3/5*3H, s), 3.38 (2/5*3H, s), 7.14-7.18 (4/5*1H, m), 7.37-7.41
(8/5*1H, m), 7.50-7.52 (5/5*1H, m), 7.72 (2/5*1H, s), 7.83-7.86
(8/5*1H, m), 7.95 (3/5*1H, s), 8.05-8.07 (4/5*1H, m), 8.14-8.17
(6/5*1H, m), 8.30 (2/5*1H, s), 8.51-8.53 (5/5*1H, m), 8.57 (3/5*1H,
s). 8-804 .delta. 3.31 (3H, s), 7.30-7.33 (1H, m), 7.48-7.52 (3H,
m), 7.56-7.60 (1H, m), 7.72-7.74 (1H, m), 7.86-7.91 (3H, m), 8.06
(1H, s), 8.22 (2H, s). 8-824 (DMSO-d.sub.6) .delta. 3.32 (12/13*3H,
s), 3.43 (1/13*3H, s), 7.01-7.02 (1/13*1H, m), 7.20-7.21 (1/13*1H,
m), 7.28 (12/13*1H, d, J = 7.8 Hz), 7.50 (12/13*1H, t, J = 7.8 Hz),
7.60-7.61 (1/13*1H, m), 7.65 (12/13*1H, t, J = 7.8 Hz), 7.83-7.84
(13/13*1H, m), 7.85 (1/13*1H, d, J = 1.5 Hz), 7.94 (12/13*1H, d, J
= 1.5 Hz), 8.10-8.12 (12/13*1H, m), 8.14 (1/13*2H, s), 8.21-8.22
(1/13*1H, m), 8.23 (12/13*2H, s), 8.32-8.35 (13/13*1H, m),
8.47-8.48 (13/13*1H, m), 10.05 (1/13*1H, s), 10.37 (12/13*1H, s).
8-840 .delta. 3.30 (10/11*3H, s), 3.43 (1/11*3H, s), 7.17-7.18
(1/11*1H, m), 7.19-7.20 (1/11*1H, m), 7.33-7.42 (22/11*1H, m), 7.52
(10/11*1H, t, J = 7.8 Hz), 7.71 (1/11*1H, s), 7.75 (10/11*1H, s),
7.87 (10/11*1H, d, J = 8.3 Hz), 8.12-8.13 (1/11*1H, m), 8.14
(1/11*2H, s), 8.17 (10/11*1H, dd, J = 2.0, 7.8 Hz), 8.23 (10/11*2H,
s), 8.47-8.50 (11/11*1H, m), 8.52-8.53 (11/11*1H, m). 9-270 .delta.
2.64 (3/4*3H, s), 3.28 (1/4*3H, s), 3.37 (1/4*3H, s), 3.56 (3/4*3H,
s), 6.70-6.71 (1/4*1H, m), 6.80-6.81 (1/4*1H, m), 7.02-7.03
(4/4*1H, m), 7.16-7.26 (16/4*1H, m), 7.34-7.36 (10/4*1H, m),
7.39-7.40 (1/4*1H, m), 7.46 (3/4*1H, t, J = 7.8 Hz), 7.80 (1/4*1H,
s), 7.91 (3/4*1H, s), 8.01 (1/4*1H, s), 8.11 (3/4*1H, s). 9-290
.delta. 2.88 (2/3*3H, s), 3.33 (1/3*3H, s), 3.37 (1/3*3H, s), 3.56
(2/3*3H, s), 6.70-6.71 (1/3*1H, m), 6.95-6.98 (2/3*1H, m), 7.10
(2/3*1H, s), 7.28-7.42 (9/3*1H, m), 7.47-7.60 (6/3*1H, m),
7.62-7.63 (4/3*1H, m), 7.86 (1/3*1H, s), 7.93 (2/3*1H, s), 8.08
(1/3*1H, s), 8.14 (2/3*1H, s). 9-291 .delta. 2.82 (2/3*3H, s), 3.30
(1/3*3H, s), 3.37 (1/3*3H, s), 3.56 (2/3*3H, s), 6.75-6.76 (1/3*1H,
m), 6.95 (1/3*1H, t, J = 7.8 Hz), 7.00-7.01 (1/3*1H, m), 7.06
(2/3*1H, s), 7.28-7.32 (4/3*1H, m), 7.39-7.54 (15/3*1H, m), 7.83
(1/3*1H, s), 7.93 (2/3*1H, s), 8.04 (1/3*1H, s), 8.14 (2/3*1H, s).
9-306 .delta. 2.89 (2/3*3H, s), 3.30 (1/3*3H, s), 3.36 (1/3*3H, s),
3.57 (2/3*3H, s), 6.96-6.97 (1/3*1H, m), 7.04-7.05 (2/3*1H, m),
7.13-7.17 (2/3*1H, m), 7.27-7.41 (10/3*1H, m), 7.60-7.63 (3/3*1H,
m), 7.81 (1/3*1H, s), 7.94 (2/3*1H, s), 8.02 (1/3*1H, s), 8.15
(2/3*1H, s), 8.24-8.25 (3/3*1H, m). 9-2164 .delta. 2.18-2.19 (3H,
m), 3.48 (3H, s), 7.21-7.25 (4H, m), 7.32-7.40 (4H, m), 7.92 (1H,
s), 8.13 (1H, s). 9-2322 .delta. 2.71-2.72 (3H, m), 3.47 (3H, s),
6.95-6.96 (1H, m), 7.11-7.16 (3H, m), 7.38-7.39 (2H, m), 7.95 (1H,
s), 8.02 (1H, s), 8.34 (1H, s). 11-777 .delta. 4.88 (2H, s),
7.20-7.21 (1H, m), 7.36 (1H, t, J = 7.8 Hz), 7.84-7.87 (1H, m),
7.92 (1H, s), 8.14-8.17 (2H, m), 8.36 (1H, broad-s). 11-835 .delta.
4.88 (2H, s), 7.22-7.23 (1H, m), 7.36 (1H, t, J = 7.8 Hz),
7.85-7.88 (1H, m), 7.95 (1H, s), 8.19 (1H, d, J = 13.1 Hz),
8.36-8.37 (2H, m).
12-777 .delta. 3.39 (3H, s), 4.74 (2H, broad-s), 7.37 (1H, t, J =
7.8 Hz), 7.52-7.56 (1H, m), 7.92 (1H, s), 8.11-8.14 (2H, m), 8.25
(1H, d, J = 14.1 Hz). 12-835 .delta. 3.40 (3H, s), 4.74 (2H,
broad-s), 7.37 (1H, t, J = 7.8 Hz), 7.55-7.58 (1H, m), 7.95 (1H,
s), 8.12-8.13 (1H, m), 8.28-8.31 (1H, m), 8.36 (1H, s). 12-864
.delta. 3.40 (3H, s), 4.74 (2H, broad-s), 7.37 (1H, t, J = 7.8 Hz),
7.52-7.58 (1H, m), 7.93 (1H, s), 8.12-8.15 (1H, m), 8.28-8.34 (2H,
m). 17-1103 .delta. 3.65 (3H, s), 7.28-7.41 (6H, m), 7.77 (1H, t, J
= 7.8 Hz), 7.91 (1H, s), 8.00-8.02 (1H, m), 8.14 (1H, s), 9.39 (1H,
s). 22-435 .delta. 3.63 (3H, s), 4.90 (2H, s), 7.92-7.97 (2H, m),
8.08-8.15 (3H, m), 9.72 (1H, s). 27-627 .delta. 3.72 (3H, s),
7.51-7.60 (5H, m), 7.90 (1H, s), 8.05 (1H, s), 8.14 (1H, s), 9.11
(1H, s). 27-628 .delta. 3.67 (3H, s), 6.99-7.24 (1H, m), 7.29-7.35
(1H, m), 7.52-7.59 (2H, m), 7.90 (1H, s), 8.06 (1H, s), 8.14 (1H,
s), 9.08 (1H, s). 27-663 .delta. 3.63 (3H, s), 7.44-7.47 (1H, m),
7.80 (1H, dd, J = 2.0, 7.8 Hz), 7.90 (1H, s), 8.10 (1H, s), 8.14
(1H, s), 8.58-8.60 (1H, m), 9.04 (1H, s). 32-247 .delta. 3.77-3.78
(3H, m), 4.96 (2H, s), 7.90 (1H, s), 8.00 (1H, s), 8.14 (1H, s),
9.02 (1H, s).
[0498] The pest control agent including the compound of the present
invention as an active ingredient can effectively control, at a low
concentration thereof, any pests such as insects including various
agricultural pests damaging agricultural/horticultural crops,
trees, and the like, insanitary pests adversely affecting the
living environment of humans such as houses and the like in various
manners, stored grain pests damaging grain and the like stored in a
warehouse, wood-eating pests damaging wood such as buildings and
the like, and mites, crustaceans, mollusks, and nematodes which
propagate and cause damage in a manner similar to that in the case
of the insects.
[0499] Specific examples of the insects, the mites, the
crustaceans, mollusks and nematodes which can be controlled using
the compound of the present invention include lepidopteran insects
such as Adoxophyes honmai, Adoxophyes orana faciata, Archips
breviplicanus, Grapholita inopinata, Archips fuscocupreanus,
Grapholita molesta, Choristoneura magnanima, Leguminivora
glycinivorella, Olethreutes mori, Caloptilia zachrysa, Argyresthia
conjugella, Spulerrina astaurota, Matsumuraeses phaseoli, Pandemis
heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Carposina
niponensis, Lyonetia prunifoliella malinella, Caloptilia theivora,
Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis
sapporensis, Acrolepiopsis suzukiella, Plutella xylostella,
Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora
gossypiella, Carposina sasakii, Chilo suppressalis, Cnaphalocrocis
medinalis, Ephestia elutella, Conogethes punctiferalis, Diaphania
indica, Etiella zinckenella, Glyphodes pyloalis, Scirpophaga
incertulas, Hellula undalis, Ostrinia furnacalis, Ostrinia
scapulalis, Parapediasia teterrella, Parnara guttata, Pieris
brassicae, Pieris rapae crucivora, Papilio xuthus, Ascotis
selenaria, Pseudoplusia includens, Euproctis pseudoconspersa,
Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra
imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon,
Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Cydla
pomonella, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa
zea, Heliothis virescens, Ostrinia nubilalis, Mamestra brassicae,
Mythimna separata, Sesamia inferens, Naranga aenescens, Spodoptera
eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera
littoralis, Spodoptera litura, Spodoptera depravata, Trichoplusia
ni, Endopiza viteana, Manduca quinquemaculata, Manduca sexta, and
the like;
[0500] Hemipteran insects such as Arboridia apicalis, Balclutha
saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca
nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles
striifrons, Nephotettix cinctinceps, Psuedatomoscelis seriatus,
Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera,
Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus,
Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri,
Trialeurodes vaporariorum, Aleurolobus taonabae, Viteus vitifolii,
Lipaphis erysimi, Aphis gossypii, Aphis spiraecola, Myzus persicae,
Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi,
Phenacoccus solani, Pulvinaria aurantii, Planococcus citri,
Pseudaonidia duplex, Planococcus kuraunhiae, Pseudococcus
comstocki, Comstockaspis perniciosa, Ceroplastes ceriferus,
Ceroplastes rubens, Aonidiella aurantii, Fiorinia theae,
Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis
prunicola, Unaspis euonymi, Unaspis yanonensis, Cimex lectularius,
Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris
lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha
halys, Nezara antennata, Nezara viridula, Piezodorus hybneri,
Plautia crossota, Scotinophora lurida, Cletus punctiger,
Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus,
Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus,
Stephanitis pyrioides, Halticus insularis, Lygus lineolaris,
Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus
caelestialium, and the like;
[0501] Coleopteran insects such as Anomala cuprea, Anomala
rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica,
Lepinotarsa decemlineata, Epilachna varivestis, Melanotus fortnumi,
Melanotus tamsuyensis, Lasioderma serricorne, Lyctusbrunneus,
Tomicus piniperda, Rhizopertha dominica, Epuraea domino, Epilachna
varivestis, Epilachna vigintioctopunctata, Tenebrio molitor,
Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus,
Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus
chinensis, Aulacophora femoralis, Oulema oryzae, Chaetocnema
concinna, Diabrotica undecimpunctata, Diabrotica virgifera,
Diabrotica barberi, Phyllotreta striolata, Psylliodes
angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus
grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera
postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus,
Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus
vestitus, Paederus fuscipes, and the like;
[0502] Thysanopteran insects such as Frankliniella intonsa, Thrips
flavus, Frankliniella occidentalis, Heliothrips haemorrhoidalis,
Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Ponticulothrips
diospyrosi, and the like;
[0503] Dipterous insects such as Asphondylia yushimai, Sitodiplosis
mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis
capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae,
Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis,
Liriomyza sativae, Liriomyza trifolii, Delia platura, Delia
antique, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola
destructor, Musca domestica, Stomoxys calcitrans, Melophagus
ovines, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina
palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus
trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis,
Culex pipiens pallens, Aedes aegypti, Aedes albopicutus, Anopheles
hyracanus sinesis, and the like;
[0504] Hymenopteran insects such as Apethymus kuri, Athalia rosae,
Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton
burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina,
Myrmecia spp., Solenopsis spp., Monomorium pharaonic, and the
like;
[0505] Orthopteran insects such as Teleogryllus emma, Gryllotalpa
orientalis, Locusta migratoria, Oxya yezoensis, Schistocerca
gregaria, and the like;
[0506] Collembolan insects such as Onychiurus folsomi, Onychiurus
sibiricus, Bourletiella hortensis, and the like;
[0507] Dictyopteran insects such as Periplaneta fuliginosa,
Periplaneta japonica, Blattella germanica, Periplaneta Americana,
and the like;
[0508] Isopterous insects such as Coptotermes formosanus,
Reticulitermes speratus, Odontotermes formosanus, and the like;
[0509] Isopterous insects such as Ctenocephalidae felis,
Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans,
Xenopsylla cheopis, and the like;
[0510] Mallophaga insects such as Menacanthus stramineus, Bovicola
bovis, and the like;
[0511] Anoplura insects such as Haematopinus eurysternus,
Haematopinus suis, Linognathus vituli, Solenopotes capillatus, and
the like;
[0512] Tarsonemidae such as Phytonemus pallidus,
Polyphagotarsonemus latus, Tarsonemus bilobatus, and the like;
[0513] Eupodidae such as Penthaleus etythrocephalus, Penthaleus
major, and the like;
[0514] Tetranychidae such as Oligonychus shinkajii, Panonychus
citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai,
Tetranychus urticae, and the like;
[0515] Eriophydae such as Acaphylla theavagrans, Aceria tulipae,
Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali,
Eriophyes chibaensis, Phyllocoptruta oleivora, and the like;
[0516] Acaridae such as Rhizoglyphus robini, Tyrophagus
putrescentiae, Tyrophagus similis, and the like;
[0517] Varroidae such as Varroa jacobsoni, and the like;
[0518] Ixodidae such as Boophilus microplus, Rhipicephalus
sanguineus, Haemaphysalis longicornis, Haemophysalis flava,
Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus,
Amblyomma spp., spp., and the like;
[0519] Cheyletidae such as Cheyletiella yasguri, Cheyletiella
blakei, and the like;
[0520] Demodicidae such as Demodex canis, Demodex cati, and the
like;
[0521] Psoroptidae such as Psoroptes ovis, and the like;
[0522] Sarcoptidae such as Sarcoptes scabiei, Notoedres cati,
Knemidocoptes spp., and the like;
[0523] Crustacea such as Armadillidium vulgare, and the like;
[0524] Gastropoda such as Pomacea canaliculata, Achatina fulica,
Meghimatium bilineatum, Limax Valentiana, Acusta despecta
sieboldiana, Euhadra peliomphala, and the like; and
[0525] Nematoda such as Prathylenchus coffeae, Prathylenchus
penetrans, Prathylenchus vulnus, Globodera rostochiensis,
Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita,
Aphelenchoides besseyi, Bursaphelenchus xylophilus, and the like,
but the present invention is not limited thereto.
[0526] The pest control agent including the compound according to
the present invention as an active ingredient has a significant
control effect against the above-described harmful crops which
damage lowland crops, upland crops, fruit trees, vegetables, and
other crops and ornamental flowers, and therefore, the effect as a
pest control agent of the present invention can be obtained by
treating the paddy field water, plant stems and leaves, or soil of
the crops of lowland, upland, fruit trees, vegetables, other crops,
ornamental flowers, and the like during the seasons in which the
appearance of such pests is expected, or before or at the point
when the pest appearance is observed.
[0527] The pest control agent including the compound according to
the present invention as an active ingredient has a significant
control effect against stored grain pests and the like generated
during storage of the harvest. That is, the pest control agent
having the compound of the present invention as an active
ingredient may be subjected to a treatment after the harvest (post
harvest) such as spray-spreading, coating, dipping, dressing,
fumigation/smoking, pressurized injection, and the like with
respect to the harvest or the place for storage of the harvest.
[0528] Further, the pest control agent including the compound
according to the present invention as an active ingredient can be
applied to plant seeds to prevent the damage caused by pests
generated in the plants after seeding. That is, the pest control
agent having the compound of the present invention as an active
ingredient may be subjected to a treatment such as spray-spreading,
dipping, dressing, and the like on the plant seeds in an effective
amount for controlling the pests as it is, as an adequate dilution
with water or the like, or as a suspension to bring the compound of
the present invention into contact with the plant seeds.
[0529] The plant seeds refer to those used for breeding in
agriculture by storing the nutrients for seedling germination, and
examples thereof include seeds such as corn, soybeans, red beans,
cotton, rice, sugar beet, wheat, barley, sunflower, tomato,
cucumber, eggplant, spinach, sting beans, squash, sugarcane,
tobacco, pimento, canola, and the like, seed tubers such as taro,
potato, sweet potato, konjac, and the like, bulbs such as edible
lily, tulips, and the like, and seed balls such as rakkyo and the
like.
[0530] The pest control agent having the compound of the present
invention as an active ingredient has a significant control effect
against insanitary pests such as Diptera pests (Culex pipiens
pallens, Culex pipiens, Chironomidae, houseflies, sandflies,
horsefly, and the like) Dictyoptera pests (Blattella germanica,
Periplaneta fuliginosa, Periplaneta americana, and the like), and
other pests.
[0531] The pest control agent having the compound of the present
invention as an active ingredient has a significant control effect
against wood-feeding pests such as termites, Lyctusbrunneus,
Rhizopertha dominica, Anobiidae, Cerambycidae, and the like, thus,
the above-described wood-feeding pests can be controlled by
treatment of wood, soil, buildings, and the like with the pest
control agent.
[0532] Since the compound of the present invention exhibits a
control effect against various pests and also exhibits an effect of
protecting useful crops and an excellent control effect as a
pesticide or a miticide at a low dose, it has an effect of
contributing to reduction in an environmental impact. In addition,
the compound of the present invention also exerts an excellent
control effect when used in combination with other
agricultural/horticultural pesticides, miticides, nematocides,
fungicides, herbicides, plant growth regulators, biological
agricultural chemicals, or the like.
[0533] For the use of the compound of the present invention, the
compound can be put to practical use as a preparation in any form
such as a soluble concentrate, an emulsifiable concentrate, a
wettable powder, a water-soluble powder, a water dispersible
granule, a water-soluble granule, a suspension concentrate, a
concentrated emulsion, a suspoemulsion, a microemulsion, a dustable
powder, a granule, a tablet, and an emulsifiable gel, typically by
mixing the compound with a suitable solid carrier or liquid
carrier, further if desired by adding to the resultant mixture, a
surfactant, a penetrant, a spreader, a thickener, an antifreezing
agent, a binder, an anticaking agent, a disintegrant, a defoaming
agent, an antiseptic or a stabilizer. In addition, from the
labor-saving and safety-enhancing viewpoints, the compound can be
put to use by encapsulating the above preparation in any form in a
water-soluble packaging material such as a water-soluble capsule
and a bag of water-soluble film
[0534] The inert carrier which can be used in the present invention
may be solids or liquids, and examples thereof include soybean
powders, grain powders, wood powders, bark powders, sawdust
powders, tobacco stem powders, walnut shell powders, brans,
cellulose powders, residues from plant extraction, synthetic
polymers such as pulverized synthetic resins, clays (for example,
kaolin, bentonite, acidic white clay), talcs (for examples, talc,
pyrophyllite, etc.), silica (for examples, diatomaceous earth,
sand, mica, white carbon [hydrous silica powders, synthetic high
dispersity silicates called hydrous silicate, there are also
products containing calcium silicate as a main component]),
activated carbon, sulfur powder, pumice, calcined diatomaceous
powders, pulverized bricks, fly ash, sand, inorganic mineral
powders such as calcium carbonate, calcium phosphate, and the like,
chemical fertilizers such as ammonium sulfate, ammonium phosphate,
ammonium nitrate, urea, ammonium chloride, and the like, a compost,
and others, which are used alone or as a mixture of two or more
kinds thereof.
[0535] Materials which can be used as the liquid inert carrier are
selected from those having the function as solvent, as well as
those capable of dispersing the active ingredient compound with the
aid of an adjuvant even if the inert carrier does not have a
function as a solvent. Representative examples thereof include the
carriers listed below: water, alcohols (for example, methanol,
ethanol, isopropanol, butanol, ethylene glycol, and the like),
ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl
ketone, diisobutylketone, cyclohexanone, and the like), ethers (for
example, diethyl ether, dioxane, cellosolve, diisopropyl ether,
tetrahydrofuran, and the like), aliphatic hydrocarbons (for
example, kerosene, mineral oil, and the like), aromatic
hydrocarbons (for example, benzene, toluene, xylene, solvent
naphtha, alkyl naphthalene, and the like), halogenated hydrocarbons
(for example, dichloromethane, chloroform, tetrachlorocarbon,
chlorobenzene, and the like), esters (for example, ethyl acetate,
butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl
phthalate, dioctyl phthalate, and the like), amides (for example,
dimethyl formamide, diethyl formamide, dimethyl acetamide, and the
like), and nitriles (for example, acetonitrile, and the like),
which are used alone or as mixtures of two or more kinds
thereof.
[0536] These solid and liquid carriers may be used alone or in a
combination of two or more kinds thereof.
[0537] Examples of the surfactant include nonionic surfactants such
as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or
di-)phenyl ethers, polyoxyethylene (mono-, di-, or tri-)styryl
phenyl ethers, polyoxyethylene-polyoxypropylene block copolymers,
polyoxyethylene aliphatic acid (mono- or di-) esters, sorbitan
aliphatic acid esters, polyoxyethylene sorbitan aliphatic acid
esters, castor oil ethylene-oxide adducts, acetylene glycol,
acetylene alcohols, acetylene glycol ethylene-oxide adducts,
acetylene alcohol ethylene-oxide adducts, alkylglucosides, and the
like; anionic surfactants such as alkyl sulfate ester salts,
alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates,
naphthalene sulfonates, alkylnaphthalene sulfonates, salts of
naphthalene sulfonate formalin condensate, salts of
alkylnaphthalene sulfonate formalin condensate,
polyoxyethylenealkylether sulfate or phosphate esters salts,
polyoxyethylene (mono- or di-) allylphenyl ether sulfate or
phosphate esters, polyoxyethylene (mono-, di-, or tri-)
styrylphenyl ether sulfate or phosphate esters, polycarboxylic acid
salts (such as polyacrylic acid salts, polymaleic acid salts,
maleic acid-olefin copolymers, and the like), polystyrene
sulfonates, and the like; cationic surfactants such as alkylamine
salts, alkyl quaternary ammonium salts, and the like; amphoteric
surfactants such as amino acid-type surfactants, betaine-type
surfactants, and the like; silicone-based surfactants; and
fluorinated surfactants.
[0538] The content of these surfactants is not particularly
limited, but it is preferably in the range of usually 0.05 part by
weight to 20 parts by weight, with respect to 100 parts by weight
of the preparation of the present invention. In addition, these
surfactants may be used alone or in combination of two or more
kinds thereof.
[0539] In order to control various pests, an amount effective for
blight control can be applied as it is or as an adequate dilution
with water or the like, or as a suspension, to the crops on which
appearance of the corresponding pests is expected or to places
where such occurrence is not preferable. The amount of use depends
on various factors such as, for example, the purpose, the pest to
be controlled, the state of plant growth, trends in pest
appearance, climate, environmental conditions, Formulation, method
of use, place of use, timing of use, and the like, but it is
preferable to use the active ingredient in the concentration of
0.0001 ppm to 5000 ppm, and preferably 0.01 ppm to 1000 ppm. The
dose that can be used per 10 a is generally in the range of 1 g to
300 g of the active ingredient.
[0540] The amount of the active ingredient of the compound of the
present invention is usually 0.1% by weight to 20% by weight for
powders, 5% by weight to 50% by weight for emulsifiable
concentrates, 3% by weight to 90% by weight for wettable powders,
0.1% by weight to 20% by weight for granules, 5% by weight to 90%
by weight for flowable Formulations, or 3% by weight to 90% by
weight for water dispersible granules. The amount of the carrier in
each form is usually 60% by weight to 99.9% by weight for powders,
40% by weight to 95% by weight for emulsifiable concentrates, 10%
by weight to 90% by weight for wettable powders, 80% by weight to
99.9% by weight for granules, 10% by weight to 95% by weight for
flowable Formulations, or 10% by weight to 90% by weight for water
dispersible granules. Further, the amount of the adjuvant is
usually 0.1% by weight to 20% by weight for powders, 1% by weight
to 20% by weight for emulsifiable concentrates, 0.1% by weight to
20% by weight for wettable powders, 0.1% by weight to 20% by weight
for granules, 0.1% by weight to 20% by weight for flowable
Formulations, and 0.1% by weight to 20% by weight for water
dispersible granules.
[0541] When the compound of the present invention is used as an
agricultural chemical, it may be used, if required, as a mixture
with other herbicides, various pesticides, miticides, nematocides,
fungicides, plant growth regulators, synergists, fertilizers, soil
conditioners, or the like to be applied during the preparation or
the dusting.
[0542] All literature, patent applications, and technical
specifications cited in the present specification are herein
incorporated by reference as if each such individual piece of
literature, patent application, and technical specification were
specifically and individually indicated to be incorporated herein
by reference.
EXAMPLES
[0543] Representative Examples of the present invention will be
described with reference to the following Examples, but the present
invention is not limited thereto. In the present Examples, DMF
means N,N-dimethyl formamide, THF means tetrahydrofuran, IPE means
isopropyl ether, DMI means 1,3-dimethyl-2-imidazolidinone, and DMSO
means dimethylsulfoxide.
[0544] Furthermore, "%" is based on mass unless specified
otherwise.
Example 1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(N-methylbenzamide)benzamide (Compound No. 7-1574).
##STR00123##
[0545] 1-1
Preparation of
4-(perfluoropropan-2-yl)-2-(trifluoromethyl)aniline
##STR00124##
[0547] 100 g (0.608 mol) of 2-(trifluoromethyl)aniline, 131 g
(0.639 mol) of 85% sodium hydrosulfite, and 20.9 g (0.0608 mol) of
tetrabutylammonium hydrogen sulfate were charged to a mixed
solution of 1500 ml of ethyl acetate and 1500 ml of water, and 53.9
g (0.639 mol) of sodium hydrogen carbonate was added thereto. 198 g
(0.669 mol) of heptafluoroisopropyl iodide was added dropwise
thereto at room temperature, followed by stirring at room
temperature for 6 hours. After the liquid separation, the solvent
of the organic layer was evaporated under reduced pressure, and 500
ml of ethyl acetate was charged thereto. 160 g (0.608 mol) of a 4 M
hydrogen chloride/ethyl acetate solution was added dropwise
thereto, followed by stirring at room temperature for 30 minutes,
and then stirring at 5.degree. C. for 1 hour. After the filtration,
the filtrate was washed with water and a saturated aqueous sodium
hydrogen carbonate in this order, and then dried over anhydrous
magnesium sulfate, and the solvent was evaporated under reduced
pressure. The obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=10:1) to
prepare 60.0 g (yield 30%) of a target compound.
[0548] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.49 (2H, broad-s),
6.81 (1H, d, J=8.3 Hz), 7.48 (1H, d, J=8.3 Hz), 7.64 (1H, s).
1-2
Preparation of
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
##STR00125##
[0550] 100 g (0.273 mol) of
4-(perfluoropropan-2-yl)-2-(trifluoromethyl)aniline was charged to
500 ml of DMF, and 52.1 g (0.287 mol) of N-bromosuccinimide was
charged in separate portions thereto over 30 minutes. After
stirring at 60.degree. C. for 2 hours, and then cooling to room
temperature, the mixture was discharged to 2000 ml of water. The
mixture was extracted with ethyl acetate, then washed with
saturated brine, and dried over anhydrous magnesium sulfate. The
solvent was evaporated under reduced pressure and the obtained
residue was purified by silica gel column chromatography (eluent
solvent; hexane:ethyl acetate=20:1) to prepare 89.0 g (yield 80%)
of a target compound.
[0551] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.03 (2H, broad-s),
7.61 (1H, s), 7.79 (1H, s).
1-3
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloro-3-
-nitrobenzamide
##STR00126##
[0553] 3.60 g (8.82 mmol) of
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline was
charged to 20 ml of anhydrous THF, and cooled to -70.degree. C.
under a nitrogen atmosphere. 4.85 ml (9.70 mmol) of a 2.0 M lithium
diisopropyl amide hexane solution was added dropwise thereto, then
2.34 g (10.7 mmol) of acid chloride which was prepared from
2-chloro-3-nitrobenzoic acid and thionyl chloride was dissolved in
5 ml of anhydrous THF, and was added dropwise thereto, followed by
stirring at -70.degree. C. for 30 minutes and then stirring at room
temperature for 30 minutes. The mixture was discharged to an
aqueous ammonium chloride solution, then extracted with ethyl
acetate, and dried over anhydrous magnesium sulfate. The solvent
was evaporated under reduced pressure and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1.fwdarw.8:2.fwdarw.3:1) to prepare 1.76 g
(yield: 34%) of a target compound.
[0554] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.61 (1H, t, J=7.8
Hz), 7.67 (1H, broad-s), 7.93-7.97 (3H, m), 8.18 (1H, broad-s).
1-4
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-nitrobenzamide
##STR00127##
[0556] To a solution of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloro-3-
-nitrobenzamide 4.89 g (8.27 mmol) in 50 ml of anhydrous DMF was
added 2.40 g (41.3 mmol) of potassium fluoride (spray-dried
product) under a flow of nitrogen, followed by stirring at
130.degree. C. for 10 hours. Liquid separation was carried out by
adding ethyl acetate, hexane, and water to the reaction mixture,
and then the organic layer was washed with water and saturated
brine, and dried over anhydrous magnesium sulfate. The solvent was
evaporated under reduced pressure and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1) to prepare 0.940 g (yield 20%) of a
target compound.
[0557] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.53 (1H, t, J=7.3
Hz), 7.93 (1H, broad-s), 8.17-8.18 (2H, m), 8.28-8.32 (1H, m),
8.44-8.48 (1H, m).
1-5
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2--
fluorobenzamide
##STR00128##
[0559] 0.940 g (1.63 mmol) of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-nitrobenzamide and 0.960 g (5.05 mmol) of stannous chloride
(anhydrous) were added to 10 ml of ethanol, and 1.02 ml (9.78 mmol)
of concentrated hydrochloric acid was added thereto, followed by
stirring at 60.degree. C. for 4 hours. The reaction mixture was
adjusted to pH 10 by the addition of an aqueous sodium hydroxide
solution, and the precipitated insolubles were removed by
filtration using Celite. The filtrate on Celite was washed with
ethyl acetate. The filtrate was extracted with ethyl acetate, and
the organic layer was washed with a 20% aqueous sodium hydroxide
solution and saturated brine, and then dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=4:1) to
prepare 0.930 g (yield 99%) of a target compound.
[0560] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.49 (1H, m), 7.91
(1H, s), 8.14 (1H, s), 8.28 (1H, d, J=14.6 Hz).
1-6
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(methylamino)benzamide
##STR00129##
[0562] 0.930 g (1.71 mmol) of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2--
fluorobenzamide was added to 5 ml of concentrated sulfuric acid,
and 10 ml of a 37% aqueous formaldehyde solution was charged
dropwise thereto at 40.degree. C. The reaction mixture was poured
into ice-water, adjusted to pH 10 using an aqueous sodium hydroxide
solution, and extracted with the addition of ethyl acetate. The
organic layer was washed with a 20% aqueous sodium hydroxide
solution and saturated brine, and then dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=8:1) to
prepare 0.690 g (yield 72%) of a target compound.
[0563] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.94 (3H, s), 4.14
(1H, broad-s), 6.88-6.93 (1H, m), 7.18 (1H, t, J=7.8 Hz), 7.37-7.41
(1H, m), 7.90 (1H, s), 8.13 (1H, s), 8.27 (1H, d, J=14.6 Hz).
[1-7] Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(N-methylbenzamide)benzamide (Compound No. 7-1574)
##STR00130##
[0565] To a solution of 1.54 g (2.75 mmol) of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(methylamino)benzamide and 0.330 g (4.13 mmol) of pyridine in 5 ml
of THF was added 0.460 g (3.30 mmol) of benzoyl chloride, followed
by stirring at 60.degree. C. for 5 hours. To the reaction mixture
were added water and ethyl acetate, and the organic layer was
washed with 1 M hydrochloric acid, a saturated aqueous sodium
hydrogen carbonate solution, and saturated brine, and then dried
over anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure and the obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=8:1), and the obtained solid was washed with IPE to prepare
1.45 g (yield 80%) of a target compound.
[0566] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.50 (3H, s),
6.99-7.33 (6H, m), 7.43-7.45 (1H, m), 7.90 (1H, s), 7.97-8.06 (2H,
m), 8.13 (1H, s).
Example 2
Preparation of
2-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-flu-
orophenyl)nicotinamide (Compound No. 6-1140)
##STR00131##
[0567] 2-1
Preparation of 4-(perfluoropropan-2-yl)aniline
##STR00132##
[0569] 100 g (1.02 mol) of aniline, 230 g (1.12 mol) of 85% sodium
hydrosulfite, and 35.1 g (0.100 mol) of tetrabutylammonium hydrogen
sulfate were charged to a mixed solution of 1500 ml of t-butyl
methyl ether and 1500 ml of water, and 94.7 g (1.12 mol) of sodium
hydrogen carbonate was added thereto. 350 g (1.12 mol) of
heptafluoroisopropyl iodide was added dropwise thereto at room
temperature, followed by stirring at room temperature for 6 hours.
After the liquid separation, the organic layer was washed with 1 M
hydrochloric acid, water, and a saturated aqueous sodium hydrogen
carbonate solution, and then dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure, and 500 ml of
ethyl acetate was charged thereto. 255 g (1.02 mol) of a 4 M
hydrogen chloride/ethyl acetate solution was added dropwise
thereto, followed by stirring at room temperature for 30 minutes
and at 5.degree. C. for 1 hour. The precipitated solid was
separated by filtration, and the solid was charged to 1000 ml of
ethyl acetate, adjusted to pH 8 to 9 by the addition of 1000 ml of
a saturated aqueous sodium hydrogen carbonate solution at
20.degree. C. or lower, and subjected to liquid separation. The
organic layer was dried over anhydrous sodium sulfate, and then the
solvent was evaporated under reduced pressure to prepare 188 g
(yield 71%) of a target compound.
[0570] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.69-6.74 (2H, m), 7.35 (2H, d, J=9.3 Hz).
2-2
Preparation of 2,6-dibromo-4-(perfluoropropan-2-yl)aniline
##STR00133##
[0572] 216 g (0.802 mol) of 4-(perfluoropropan-2-yl)aniline was
charged to 863 ml of DMF, followed by cooling to 5.degree. C. 285 g
(1.60 mol) of N-bromosuccinimide was charged in separate portions
thereto over 1 hour. The mixture was stirred at room temperature
for 1 hour and then stirred at 37.degree. C. for 2 hours. The
mixture was discharged to 2000 ml of water, extracted with 2000 ml
of ethyl acetate, and washed with 1000 ml of saturated brine. After
dried over anhydrous magnesium sulfate, the solvent was evaporated
under reduced pressure. The obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=20:1) to prepare 304 g (yield 90%) of a target
compound.
[0573] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.88 (2H, broad-s),
7.59 (2H, s).
2-3
Preparation of
2-chloro-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-3-nitrobenzamide
##STR00134##
[0575] According to the method of 1-3 of Example 1, a target
compound was prepared from
2,6-dibromo-4-(perfluoropropan-2-yl)aniline
[0576] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.58 (1H, t, J=7.8
Hz), 7.66 (1H, broad-s), 7.90 (2H, s), 7.93 (1H, dd, J=1.5, 7.8
Hz), 7.98 (1H, d, J=7.8 Hz).
2-4
Preparation of
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide
##STR00135##
[0578] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-3-nitrobenzamide
[0579] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.51-7.55 (1H, m);
7.90 (2H, s), 8.16 (1H, d, J=11.7 Hz), 8.27-8.31 (1H, m), 8.48 (1H,
t, J=6.3 Hz).
2-5
Preparation of
3-amino-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide
##STR00136##
[0581] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide.
[0582] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.49 (1H, m), 7.91
(1H, s), 8.14 (1H, s), 8.28 (1H, d, J=14.6 Hz).
2-6
Preparation of
2-chloro-N-(3-(2,6-dibromo-4-(perfluoropropan-2-yl)phenylcarbamoyl)-2-flu-
orophenyl)nicotinamide (Compound No. 6-1140)
##STR00137##
[0584] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide
and 2-chloronicotinic acid chloride.
[0585] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.40-7.49 (2H, m),
7.89 (2H, s), 7.94-7.96 (1H, m), 8.13 (1H, d, J=12.7 Hz), 8.32-8.34
(1H, m), 8.57-8.59 (1H, m), 8.67-8.71 (1H, m), 8.75 (1H,
broad-s).
Example 3
Preparation of
3-benzamide-2-fluoro-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenyl)benzamide (Compound No. 6-2110)
##STR00138##
[0586] 3-1
Preparation of 2,6-diiodo-4-(perfluoropropan-2-yl)aniline
##STR00139##
[0588] To a solution of 5.74 g (22.0 mmol) of
4-(perfluoropropan-2-yl)aniline obtained in 2-1 of Example 2 in 50
ml of ethanol was added 2.16 g (22.0 mmol) of concentrated sulfuric
acid at 5.degree. C. The reaction mixture was warmed to room
temperature, and 10.0 g (44.0 mmol) of N-iodosuccinimide was added
thereto, followed by stirring for 3 hours. The reaction mixture was
neutralized with a saturated aqueous sodium hydrogen carbonate
solution. The precipitated crystals were filtered, washed with
water, and then dried to prepare 9.00 g (yield 80%) of a target
compound.
[0589] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.95 (2H, broad-s),
7.79 (2H, s).
3-2
Preparation of
2-chloro-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-3-nitrobenzamide
##STR00140##
[0591] To a solution of 40.0 g (78.0 mmol) of
2,6-diiodo-4-(perfluoropropan-2-yl)aniline in 100 ml of DMI was
added 20.6 g (94.0 mmol) of 2-chloro-3-nitrobenzoyl chloride,
followed by stirring at 135.degree. C. for 3 hours. After cooling
to room temperature, the reaction mixture was poured into 1000 ml
of water. After extraction with the addition of 1000 ml of ethyl
acetate, the organic layer was washed with water and then dried
over anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure and the obtained residue was washed with hexane to
prepare 56.2 g (yield 99%) of a target compound.
[0592] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.58 (1H, t, J=8.3
Hz), 7.70 (1H, d, J=3.4 Hz), 7.93 (1H, dd, J=1.5, 6.3 Hz),
8.08-8.10 (1H, m), 8.13 (2H, s).
3-3
Preparation of
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide
##STR00141##
[0594] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-3-nitrobenzamide
[0595] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.52-7.55 (1H, m),
8.12-8.18 (3H, m), 8.29-8.32 (1H, 8.48-8.51 (1H, m).
3-4
Preparation of
3-amino-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide
##STR00142##
[0597] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide
[0598] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.08 (1H, t, J=7.8 Hz), 7.39-7.43 (1H, m), 8.10
(2H, s), 8.72 (1H, d, J=11.2 Hz).
3-5
Preparation of
3-benzamide-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzami-
de (Compound No. 6-1260)
##STR00143##
[0600] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide
[0601] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.39 (1H, t, J=7.8
Hz), 7.52-7.57 (4H, m), 7.60-7.63 (2H, m), 7.93-7.94 (4H, m), 8.70
(1H, t, J=6.3 Hz).
3-6
Preparation of
3-benzamide-2-fluoro-N-(4-(perfluoropropan-2-yl)-2,6-bis(trifluoromethyl)-
phenyl)benzamide (Compound No. 6-2110)
##STR00144##
[0603] A solution of 1.95 g (2.59 mmol) of
3-benzamide-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzami-
de, 0.10 g (0.520 mmol) of copper iodide, and 1.24 g (6.48 mmol) of
methyl fluorosulfonyl difluoroacetate in 50 ml of DMF was stirred
at 100.degree. C. for 6 hours. The reaction mixture was cooled to
room temperature, and then 10 ml of water and 100 ml of ethyl
acetate were added thereto, followed by filtration through Celite.
The organic layer of the liquid was washed with water and a
saturated aqueous sodium hydrogen carbonate solution, and then
dried over anhydrous magnesium sulfate. The solvent was evaporated
under reduced pressure and the obtained residue was purified by
silica gel column chromatography (eluent solvent; hexane:ethyl
acetate=1:1). The obtained solid was washed with hexane to prepare
0.840 g (yield 51%) of a target compound.
[0604] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.36-7.40 (1H, m),
7.53-7.64 (3H, m), 7.84-7.97 (1H, m), 7.92-7.94 (2H, m), 8.04-8.07
(1H, m), 8.08-8.13 (1H, m), 8.20 (2H, s), 8.68-8.72 (1H, m).
Example 4
Preparation of
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(N
methylbenzamide)benzamide (Compound No. 7-1182)
##STR00145##
[0605] 4-1
Preparation of 4-(perfluorobutan-2-yl)aniline
##STR00146##
[0607] 4.90 g (52.6 mmol) of aniline, 10.1 g (58.0 mmol) of 85%
sodium hydrosulfite, and 1.90 g (5.77 mmol) of tetrabutylammonium
hydrogen sulfate were charged to a mixed solution of 150 ml of
t-butyl methyl ether and 150 ml of water using a light-shielded
reaction vessel, and 4.84 g (57.6 mmol) of sodium hydrogen
carbonate was added thereto. 20.0 g (57.8 mmol) of
nonafluoro-s-butyliodide was added dropwise thereto at room
temperature, followed by stirring at room temperature for 5 hours.
The organic phase was collected by separation, washed with 2 mol/L
of an aqueous hydrochloric acid solution twice, and then washed
with saturated brine, an aqueous sodium hydrogen carbonate
solution, and saturated brine. The organic layer was dried over
anhydrous magnesium sulfate, and then the solvent was evaporated
under reduced pressure to prepare 8.32 g (yield 51%) of a target
compound.
[0608] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.72 (2H, d, J=8.8 Hz), 7.34 (2H, d, J=8.8 Hz).
4-2
Preparation of 2,6-dibromo-4-(perfluorobutan-2-yl)aniline
##STR00147##
[0610] According to the method of 2-2 of Example 2, a target
compound was prepared from 4-(perfluorobutan-2-yl)aniline.
[0611] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.89 (2H, broad-s),
7.57 (2H, s).
4-3
Preparation of
2-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide
##STR00148##
[0613] To 27 ml of DMI were added 9.90 g (21.1 mmol) of
2,6-dibromo-4-(perfluorobutan-2-yl)aniline and 4.60 g (20.9 mmol)
of 2-chloro-3-nitrobenzoyl chloride, followed by stirring at
140.degree. C. for 4 hours. To the reaction solution were added
water and ethyl acetate, and the organic phase was extracted, and
washed with 1 mol/L of an aqueous sodium hydroxide solution,
saturated brine, and dried over anhydrous magnesium sulfate. Then,
the solvent was evaporated under reduced pressure. The obtained
residue was purified by silica gel column chromatography (eluent
solvent; hexane:ethyl
acetate=20:1.fwdarw.10:1.fwdarw.5:1.fwdarw.3:1) to prepare 5.44 g
(yield 40%) of a target compound.
[0614] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.52-7.61 (2H, m),
7.89 (2H, s), 7.94 (1H, dd, J=1.5, 8.3 Hz), 7.99 (1H, d, J=7.8
Hz).
4-4
Preparation of
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide
##STR00149##
[0616] To 108 ml of DMSO were added 5.44 g (8.34 mmol) of
2-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide
and 4.90 g (84.3 mmol) of potassium fluoride (spray-dried product),
followed by stirring at 145.degree. C. for 2 hours. The reaction
solution was poured into ice-water to precipitate the crystal, and
the obtained crystals were filtered and washed with hexane. The
obtained crystals were purified by silica gel column chromatography
(eluent solvent; hexane:ethyl acetate=5:1) to prepare 2.42 g (yield
46%) of a target compound.
[0617] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.53-7.54 (1H, m),
7.89 (2H, s), 8.17 (1H, d, J=12.2 Hz), 8.29-8.30 (1H, m), 8.48-8.49
(1H, m).
4-5
Preparation of
3-amino-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluorobenzamide
##STR00150##
[0619] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide.
[0620] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.99-7.04 (1H, m), 7.11-7.12 (1H, m), 7.48-7.52 (1H, m), 7.86 (2H,
s), 8.22 (1H, d, J=14.1 Hz).
4-6
Preparation of
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(methylamino)ben-
zamide
##STR00151##
[0622] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluorobenzamide.
[0623] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.95 (3H, s), 4.14
(1H, broad-s), 6.91-6.92 (1H, m), 7.17-7.21 (1H, m), 7.39-7.43 (1H,
m), 7.85 (2H, s), 8.21 (1H, d, J=14.1 Hz).
4-7
Preparation of
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(N-methylbenzami-
de)benzamide (Compound No. 7-1182)
##STR00152##
[0625] According to the method of 1-7 of Example 1, a target
compound was prepared from
N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-2-fluoro-3-(methylamino)ben-
zamide.
[0626] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.51 (3H, s),
7.22-7.44 (7H, m), 7.85 (2H, s), 8.00-8.03 (2H, m).
Example 5
Preparation of
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-3-(4-cyanob-
enzamide)-2-fluorobenzamide (Compound No. 6-5911)
##STR00153##
[0627] 5-1
Preparation of
2-(perfluoroethyl)-4-(perfluoropropan-2-yl)aniline
##STR00154##
[0629] According to the method of 1-1 of Example 1, a target
compound was prepared from 4-(perfluoropropan-2-yl)aniline obtained
in Example 2-1 and 1,1,2,2,2-pentafluoroethyliodide.
[0630] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.56 (2H, broad-s),
6.79 (1H, d, J=8.8 Hz), 7.47 (1H, d, J=8.8 Hz), 7.53 (1H, s).
5-2
Preparation of
2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)aniline
##STR00155##
[0632] According to the method of 1-2 of Example 1, a target
compound was prepared from
2-(perfluoroethyl)-4-(perfluoropropan-2-yl)aniline.
[0633] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.14 (2H, broad-s),
7.58 (1H, s), 7.81 (1H, s).
5-3
Preparation of
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-chloro-3--
nitrobenzamide
##STR00156##
[0635] According to the method of 4-3 of Example 4, a target
compound was prepared from
2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)aniline.
[0636] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.56-7.61 (1H, m),
7.73 (1H, s), 7.88 (1H, d, J=1.5 Hz), 7.92-7.98 (2H, m), 8.21 (1H,
s).
5-4
Preparation of
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3--
nitrobenzamide
##STR00157##
[0638] According to the method of 1-4 of Example 1, a target
compound was prepared from
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-chloro-3--
nitrobenzamide
[0639] APCI-MS m/z (M+1):626
5-5
Preparation of
3-amino-N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-f-
luorobenzamide
##STR00158##
[0641] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-fluoro-3--
nitrobenzamide.
[0642] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.99-7.04 (1H, m), 7.05-7.18 (1H, m), 7.46-7.51 (1H, m), 7.85 (1H,
broad-s), 8.17 (1H, broad-s), 8.34 (1H, d, J=15.1 Hz).
5-6
Preparation of
N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-3-(4-cyanob-
enzamide)-2-fluorobenzamide (Compound No. 6-5911)
##STR00159##
[0644] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-6-(perfluoroethyl)-4-(perfluoropropan-2-yl)phenyl)-2-f-
luorobenzamide and 4-cyanobenzoylchloride.
[0645] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.41 (1H, t, J=8.3
Hz), 7.84-7.87 (3H, m), 7.91-7.95 (1H, m), 8.03-8.05 (2H, m), 8.10
(1H, broad-s), 8.17-8.20 (2H, m), 8.63-8.67 (1H, m).
Example 6
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(N-methy-
lbenzamide)picolinamide (Compound No. 17-1103)
##STR00160##
[0646] 6-1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-chloropi-
coline amide
##STR00161##
[0648] According to the method of 1-3 of Example 1, a target
compound was prepared from 2-chloropyridine-6-carboxylic acid
chloride prepared from 2-chloropyridine-6-carboxylic acid and
thionyl chloride, and
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1.
[0649] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.59 (1H, d, J=7.3
Hz), 7.90-7.93 (2H, m), 8.14 (1H, s), 8.20-8.24 (1H, m), 9.60 (1H,
s).
6-2
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(methyla-
mino)picolinamide
##STR00162##
[0651] To a solution of 0.100 g (0.180 mmol) of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-chloropi-
coline amide in 5 ml of 1,4-dioxane were added 0.00600 g (0.0360
mmol) of copper sulfate and 0.140 g (1.80 mmol) of a 40% aqueous
methylamine solution, followed by stirring at an oil bath
temperature 80.degree. C. for 3 hours under an enclosed condition.
The reaction liquid was returned to room temperature and opened,
and water and ethyl acetate were added thereto. The organic layer
was washed with water and saturated brine, and dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=2:1) to
prepare 0.0700 g (yield 69%) of a target compound.
[0652] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.64 (3H, s), 3.79
(1H, broad-s), 7.56-7.60 (1H, m), 7.87-7.93 (2H, m), 8.14-8.15 (1H,
m), 8.20-8.23 (1H, m), 9.60 (1H, s).
6-3
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(N-methy-
lbenzamide)picolinamide (Compound No. 17-1103)
##STR00163##
[0654] According to the method of 1-7 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(methyla-
mino)picolinamide.
[0655] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.65 (3H, s),
7.28-7.41 (6H, m), 7.77 (1H, t, J=7.8 Hz), 7.91 (1H, s), 8.00-8.02
(1H, m), 8.14 (1H, s), 9.39 (1H, s).
Example 7
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-(2-fluor-
o-N-methylbenzamide)thiazole-4-carboxamide (Compound No.
27-628)
##STR00164##
[0656] 7-1
Preparation of 2-aminothiazole-4-carboxylic acid
##STR00165##
[0658] To 40 ml of an aqueous solution of 4.00 g (23.2 mmol) of
ethyl 2-aminothiazole-4-carboxylate was added 1.86 g (46.5 mmol) of
sodium hydroxide, followed by stirring at room temperature for 5
hours. The reaction liquid was adjusted to pH 1 by the addition of
concentrated hydrochloric acid, and the precipitated crystals were
collected by filtration to prepare 2.84 g (yield 85%) of a target
compound.
[0659] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.18 (2H, broad-s),
7.38 (1H, s).
[0660] The proton of the carboxylic acid was not detected.
7-2
Preparation of 2-chlorothiazole-4-carboxylic acid
##STR00166##
[0662] To a solution of 2.84 g (19.7 mmol) of
2-aminothiazole-4-carboxylic acid in 30 ml of 1,4-dioxane was added
50 ml of concentrated hydrochloric acid, followed by cooling to
0.degree. C., and 10 ml of an aqueous solution of 2.04 g (29.6
mmol) of sodium nitrite was added charged dropwise thereto at
0.degree. C. to 5.degree. C. The reaction liquid was stirred at
0.degree. C. for 2 hours, and then 2.93 g (29.6 mmol) of copper
chloride was charged in separate portions thereto. The reaction
liquid was returned to room temperature, followed by stirring for 8
hours. To the reaction liquid were added water and ethyl acetate,
followed by extraction with ethyl acetate four times. The organic
layer was washed with saturated brine, and then dried over
anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure to prepare 1.77 g (yield 55%) of a target
compound.
[0663] .sup.1H-NMR (DMSO-d.sub.6, ppm) .delta. 8.41 (1H, s).
[0664] The proton of the carboxylic acid was not detected.
7-3
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloroth-
iazole-4-carboxamide
##STR00167##
[0666] According to the method of 4-3 of Example 4, a target
compound was prepared from 2-chlorothiazole-4-carbonylchloride
prepared from 2-chlorothiazole-4-carboxylic acid and thionyl
chloride, and
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1.
[0667] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.91 (1H, s), 8.13
(1H, s), 8.19 (1H, s), 8.82 (1H, s).
7-4
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-(methyla-
mino)thiazole-4-carboxamide
##STR00168##
[0669] According to the method of 6-2 of Example 6, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloroth-
iazole-4-carboxamide.
[0670] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.03 (3H, s),
5.11-5.12 (1H, m), 7.50 (1H, s), 7.88 (1H, s) 8.11 (1H, s), 8.99
(1H, s).
7-5
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-(2-fluor-
o-N-methylbenzamide)thiazole-4-carboxamide (Compound No.
27-628)
##STR00169##
[0672] According to the method of 1-7 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-(methyla-
mino)thiazole-4-carboxamide and 2-fluorobenzoyl chloride.
[0673] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.67 (3H, s),
6.99-7.24 (1H, m), 7.29-7.35 (1H, m), 7.52-7.59 (2H, m), 7.90 (1H,
s), 8.06 (1H, s), 8.14 (1H, s), 9.08 (1H, s).
Example 8
Preparation of 2,2,2-trichloroethyl
2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarba-
moyl)phenyl(methyl)carbamate (Compound No. 12-864)
##STR00170##
[0674] 8-1
Preparation of
4-(perfluorobutan-2-yl)-2-(trifluoromethyl)aniline
##STR00171##
[0676] According to the method of 1-1 of Example 1, a target
compound was prepared from 2-(trifluoromethyl)aniline and
nonafluoro-s-butyliodide under the light-shielding reaction
condition.
[0677] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.49 (2H, broad-s),
6.81 (1H, d, J=8.8 Hz), 7.47 (1H, d, J=8.8 Hz), 7.61 (1H, s).
8-2
Preparation of
2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)aniline
##STR00172##
[0679] To 100 mL of ethanol was added 17.0 g (44.8 mmol) of
4-(perfluorobutan-2-yl)-2-(trifluoromethyl)aniline, and 5.28 g
(53.8 mmol) of concentrated sulfuric acid and 12.6 g (55.8 mmol) of
N-iodosuccinimide were added thereto under ice-cooling, followed by
stirring at room temperature for 1 hour and 30 minutes and at
40.degree. C. for 4 hours. To the reaction solution was added a 4 M
aqueous sodium hydroxide solution to neutralize the reaction
solution, and then ethyl acetate was added thereto to extract the
organic phase. The organic phase was washed with saturated brine,
and dried over anhydrous magnesium sulfate, and then the solvent
was evaporated under reduced pressure. The obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1) to prepare 14.6 g (yield 65%) of a
target compound.
[0680] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.04 (2H, broad-s),
7.62 (1H, s), 7.97 (1H, s).
8-3
Preparation of
2-chloro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-n-
itrobenzamide
##STR00173##
[0682] According to the method of 4-3 of Example 4, a target
compound was prepared from
2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)aniline
[0683] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.60-7.61 (1H, m),
7.77 (1H, s), 7.89-7.96 (2H, m), 8.03-8.04 (1H, m), 8.38 (1H,
s).
8-4
Preparation of
2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-n-
itrobenzamide
##STR00174##
[0685] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-n-
itrobenzamide.
[0686] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.53-7.54 (1H, m),
7.95 (1H, s), 8.24-8.32 (2H, m), 8.36 (1H, s), 8.44-8.48 (1H,
m).
8-5
Preparation of
3-amino-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phe-
nyl)benzamide
##STR00175##
[0688] According to the method of 1-5 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-n-
itrobenzamide
[0689] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
7.02-7.03 (1H, m), 7.11-7.13 (1H, m), 7.47-7.51 (1H, m), 7.92 (1H,
s), 8.31-8.34 (2H, m).
8-6
Preparation of
2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(-
methylamino)benzamide
##STR00176##
[0691] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phe-
nyl)benzamide.
[0692] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.95-2.96 (3H, m),
4.15 (1H, broad-s), 6.91-6.93 (1H, m), 7.19-7.20 (1H, m), 7.38-7.42
(1H, m), 7.92 (1H, s), 8.32 (1H, d, J=14.1 Hz), 8.34 (1H, s).
8-7
Preparation of 2,2,2-trichloroethyl
2-fluoro-3-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenylcarba-
moyl)phenyl(methyl)carbamate (Compound No. 12-864)
##STR00177##
[0694] According to the method of 1-7 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(perfluorobutan-2-yl)-6-(trifluoromethyl)phenyl)-3-(-
methylamino)benzamide and
2,2,2-trichloroethoxycarbonylchloride.
[0695] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.40 (3H, s), 4.74
(2H, broad-s), 7.37 (1H, t, J=7.8 Hz), 7.52-7.58 (1H, m), 7.93 (1H,
s), 8.12-8.15 (1H, m), 8.28-8.34 (2H, m).
Example 9
Preparation of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3-
-(4-cyano-N-methylbenzamide)benzamide (Compound No. 2-491)
##STR00178##
[0696] 9-1
Preparation of
2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
##STR00179##
[0698] According to the method of 1-2 of Example 1, a target
compound was prepared from
4-(perfluoropropan-2-yl)-2-(trifluoromethyl)aniline obtained in 1-1
of Example 1 and N-chlorosuccinimide
[0699] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.97 (2H, broad-s),
7.57 (1H, s), 7.64 (1H, s).
9-2
Preparation of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-iodo-3--
nitrobenzamide
##STR00180##
[0701] According to the method of 1-3 of Example 1, a target
compound was prepared from 4-iodo-3-nitrobenzoyl chloride prepared
from 4-iodo-3-nitrobenzoic acid and thionyl chloride, and
2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
[0702] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.52-7.81 (2H, m),
7.89 (1H, s), 8.00 (1H, s), 8.25 (1H, d, J=8.3 Hz), 8.38 (1H, d,
J=1.9 Hz).
9-3
Preparation of
3-amino-N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-
-iodobenzamide
##STR00181##
[0704] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-iodo-3--
nitrobenzamide
[0705] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.35 (2H, s), 6.92
(1H, dd, J=1.9, 8.3 Hz), 7.29 (1H, d, J=1.9 Hz), 7.60 (1H, s), 7.79
(1H, d, J=8.3 Hz), 7.86 (1H, s), 7.97 (1H, s).
9-4
Preparation of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-iodo-3--
(methylamino)benzamide
##STR00182##
[0707] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-
-iodobenzamide
[0708] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.97 (3H, s), 4.46
(1H, broad-s), 6.89 (1H, dd, J=1.9, 8.3 Hz), 7.07 (1H, d, J=1.9
Hz), 7.65 (1H, s), 7.80 (1H, d, J=8.3 Hz), 7.86 (1H, s), 7.97 (1H,
s).
9-5
Preparation of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3-
-(methylamino)benzamide
##STR00183##
[0710] To 10 mL of DMF were added 0.350 g (0.560 mmol) of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-iodo-3--
(methylamino)benzamide and 0.200 g (2.25 mmol) of copper (I)
cyanide, followed by stirring at 140.degree. C. for 1 hour and 30
minutes. A saturated aqueous sodium thiosulfate solution was poured
into the reaction solution to quench the reaction, and the organic
layer was collected with ethyl acetate and washed with saturated
brine. The organic layer was dried over anhydrous magnesium
sulfate, and then the solvent was evaporated under reduced
pressure. The obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl
acetate=5:1.fwdarw.3:1) to prepare 0.250 g (yield 86%) of a target
compound.
[0711] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.01 (1/2*3H, s), 3.03
(1/2*3H, s), 4.89 (1/2*1H, s), 4.90 (1/2*1H, s), 7.80 (1H, dd,
J=1.5, 8.3 Hz), 7.21-7.22 (1H, m), 7.54 (1H, d, J=8.3 Hz), 7.67
(1H, s), 7.88 (1H, s), 7.99 (1H, s).
9-6
Preparation of
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3-
-(4-cyano-N-methylbenzamide)benzamide (Compound No. 2-491)
##STR00184##
[0713] According to the method of 1-7 of Example 1, a target
compound was prepared from
N-(2-chloro-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3-
-(methylamino)benzamide and 4-cyanobenzoylchloride.
[0714] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.81 (3H, broad-s),
7.52-7.84 (8H, m), 7.89 (1H, s), 8.00 (1H, s).
Example 10
Preparation of
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-6-cyano-2-fluorophenyl)-6-chloronicotinamide (Compound No.
1-1968)
##STR00185##
[0715] 10-1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-2,-
3-difluorobenzamide
##STR00186##
[0717] To a solution of 0.840 g (4.59 mmol) of
4-cyano-2,3-difluorobenzoic acid in 10 ml of dichloromethane were
added one drop of DMF and 0.470 ml (5.51 mmol) of oxalyl chloride,
followed by stirring at room temperature for 1 hour. The solvent
was evaporated under reduced pressure and the obtained
4-cyano-2,3-difluorobenzoyl chloride was added to a solution of
1.56 g (3.83 mmol) of
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1 in 5 ml of DMI, followed by stirring
at 130.degree. C. for 5 hours. To the reaction liquid were added
water and ethyl acetate, and the organic layer was washed with a
saturated aqueous sodium hydrogen carbonate solution and saturated
brine, and then dried over anhydrous magnesium sulfate. The solvent
was evaporated under reduced pressure and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=1:0.fwdarw.10:1) to prepare 0.58 g (yield 27%)
of a target compound.
[0718] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.52-7.62 (1H, m),
7.92-7.94 (1H, m), 8.02-8.06 (1H, m), 8.13-8.16 (2H, m).
10-2
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
cyano-2-fluorobenzamide
##STR00187##
[0720] To a solution of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-2,-
3-difluorobenzamide in 5 ml of DMSO was added 49.0 mg of ammonium
carbonate, followed by stirring 100.degree. C. for 5 hours. To the
reaction liquid were added water and ethyl acetate, and the organic
layer was washed with water, and then and dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl
acetate=8:1.fwdarw.4:1) to prepare 0.30 g (yield 51%) of a target
compound.
[0721] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.71 (2H, broad-s),
7.35-7.39 (1H, m), 7.40-7.44 (1H, m), 7.92 (1H, s), 8.12-8.15 (2H,
m).
10-3
Preparation of
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamoyl-
)-6-cyano-2-fluorophenyl)-6-chloronicotinamide (Compound No.
1-1968)
##STR00188##
[0723] To a solution of 0.0500 g (0.0877 mol) of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
cyano-2-fluorobenzamide in 0.200 ml of DMI was added 0.0308 g
(0.175 mmol) of 6-chloronicotinoylchloride, followed by stirring at
130.degree. C. for 6 hours. To the reaction liquid were added water
and ethyl acetate, and the organic layer was washed with 1 M
hydrochloric acid, a saturated aqueous sodium hydrogen carbonate
solution, and saturated brine, and then dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=2:1) to
prepare 0.0100 g (yield 16%) of a target compound.
[0724] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.54 (1H, d, J=8.8
Hz), 7.72 (1H, d, J=8.8 Hz), 7.93 (1H, s), 8.09 (1H, s), 8.17-8.18
(2H, m), 8.27 (1H, dd, J=2.4 Hz 8.8 Hz), 8.38 (1H, d, J=10.8 Hz),
8.98 (1H, d, J=2.4 Hz).
Example 11
Preparation of
3-(4-cyanobenzamide)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)benzamid-
e (Compound No. 6-79)
##STR00189##
[0725] 11-1
Preparation of 2,6-diiodo-4-(perfluorobutan-2-yl)aniline
##STR00190##
[0727] According to the method of 3-1 of Example 3, a target
compound was prepared from 4-(perfluorobutan-2-yl)aniline obtained
in 4-1 of Example 4.
[0728] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.95 (2H, broad-s),
7.78 (2H, s).
11-2
Preparation of
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide
##STR00191##
[0730] According to the method of 4-3 of Example 4, a target
compound was prepared from
2,6-diiodo-4-(perfluorobutan-2-yl)aniline and 3-nitrobenzoyl
chloride.
[0731] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.74 (1H, t, J=8.0
Hz), 8.11 (2H, s), 8.42 (1H, d, J=7.6 Hz), 8.46 (1H, d, J=8.4 Hz),
8.90 (1H, d, J=12.4 Hz), 8.92 (1H, s).
11-3
Preparation of
3-amino-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)benzamide
##STR00192##
[0733] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide.
[0734] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.39 (2H, broad-s),
6.89-6.93 (1H, m), 7.29-7.31 (3H, m), 7.68 (1H, s), 8.08 (2H,
s).
11-4
Preparation of
3-(4-cyanobenzamide)-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)benzamid-
e (Compound No. 6-79)
##STR00193##
[0736] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-diiodo-4-(perfluorobutan-2-yl)phenyl)benzamide and
4-cyanobenzoylchloride.
[0737] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.58 (1H, t, J=8.2
Hz), 7.79-7.83 (3H, m), 7.97 (2H, s), 8.01 (2H, d, J=8.0 Hz), 8.09
(2H, s), 8.18 (1H, s), 8.29 (1H, s).
Example 12
Preparation of
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenylcarbamoy-
l)-2-fluorophenyl)-2-chloronicotinamide (Compound No. 6-5908)
##STR00194##
[0738] 12-1
Preparation of
4-(perfluoropropan-2-yl)-2-(trifluoromethoxy)aniline
##STR00195##
[0740] According to the method of 1-1 of Example 1, a target
compound was prepared from 2-trifluoromethoxy aniline
[0741] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.19 (2H, broad-s),
6.86 (1H, d, J=8.8 Hz), 7.30 (1H, d, J=8.8 Hz), 7.36 (1H, s).
12-2
Preparation of
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)aniline
##STR00196##
[0743] According to the method of 1-2 of Example 1, a target
compound was prepared from
4-(perfluoropropan-2-yl)-2-(trifluoromethoxy)aniline
[0744] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.65 (2H, broad-s),
7.33 (1H, s), 7.71 (1H, s).
12-3
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-chloro--
3-nitrobenzamide
##STR00197##
[0746] According to the method of 1-3 of Example 1, a target
compound was prepared from
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)aniline
[0747] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.49-7.61 (3H, m),
7.80-7.96 (3H, m).
12-4
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-fluoro--
3-nitrobenzamide
##STR00198##
[0749] According to the method of 1-4 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-chloro--
3-nitrobenzamide.
[0750] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.53 (1H, t, J=7.8
Hz), 7.60 (1H, broad-s), 7.89 (1H, d, J=1.5 Hz), 8.07 (1H, broad-d,
J=12.7 Hz), 8.29-8.30 (1H, m), 8.43-8.47 (1H, m).
12-5
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-
-fluorobenzamide
##STR00199##
[0752] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-fluoro--
3-nitrobenzamide.
[0753] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.99-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.45-7.49 (1H, m), 7.57
(1H, broad-s), 7.87 (1H, d, J=2.0 Hz), 8.14 (1H, d, J=14.2 Hz).
12-6
Preparation of
N-(3-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenylcarbamoy-
l)-2-fluorophenyl)-2-chloronicotinamide (Compound No. 6-5908)
##STR00200##
[0755] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-2-
-fluorobenzamide and 2-chloronicotinoylchloride.
[0756] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.39-7.49 (2H, m),
7.59 (1H, s), 7.88-7.94 (2H, m), 8.07 (1H, d, J=12.2 Hz), 8.31-8.33
(1H, m), 8.57-8.58 (1H, m), 8.60-8.70 (1H, m), 8.74 (1H,
broad-s).
Example 13
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-4-fluorobenzamide (Compound No. 6-3348)
##STR00201##
[0757] 13-1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-
-nitrobenzamide
##STR00202##
[0759] According to the method of 1-3 of Example 1, a target
compound was prepared from 4-fluoro-3-nitrobenzoyl chloride
prepared from 4-fluoro-3-nitrobenzoic acid and thionyl chloride,
and 2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1.
[0760] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.47-7.50 (1H, m),
7.92 (2H, d, J=5.9 Hz), 8.16 (1H, s), 8.23-8.28 (1H, m), 8.65-8.67
(1H, m).
13-2
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
fluorobenzamide
##STR00203##
[0762] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-
-nitrobenzamide.
[0763] APCI-MS m/z (M+1):546
13-3
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-4-fluorobenzamide (Compound No. 6-3348)
##STR00204##
[0765] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
fluorobenzamide.
[0766] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.29-7.34 (1H, m),
7.53-7.65 (3H, m), 7.80-7.84 (1H, m), 7.90-7.92 (3H, m), 8.14 (1H,
broad-s), 8.20 (1H, d, J=2.9 Hz), 8.25 (1H, broad-s), 9.10 (1H, dd,
J=1.9, 7.3 Hz).
Example 14
Preparation of
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)nicotinamide (Compound No. 6-460)
##STR00205##
[0767] 14-1
Preparation of
2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
##STR00206##
[0769] According to the method of 8-2 of Example 8, a target
compound was prepared from
4-(perfluoropropan-2-yl)-2-(trifluoromethyl)aniline obtained in 1-1
of Example 1 and N-iodosuccinimide
[0770] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.04 (2H, broad-s),
7.64 (1H, s), 7.99 (1H, s).
14-2
Preparation of
N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-nitrobenz-
amide
##STR00207##
[0772] According to the method of 4-3 of Example 4, a target
compound was prepared from
2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline and
3-nitrobenzoyl chloride.
[0773] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.76-7.80 (2H, m),
7.97 (1H, s), 8.28-8.30 (1H, m), 8.37 (1H, s), 8.49-8.52 (1H, m),
8.78 (1H, s).
14-3
Preparation of
3-amino-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz-
amide
##STR00208##
[0775] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-nitrobenz-
amide.
[0776] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.89 (2H, broad-s),
6.89-6.92 (1H, m), 7.23-7.32 (3H, m), 7.68 (1H, s), 7.93 (1H, s),
8.34-8.36 (1H, m).
14-4
Preparation of
2-chloro-N-(3-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenylc-
arbamoyl)phenyl)nicotinamide (Compound No. 6-460)
##STR00209##
[0778] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz-
amide and 2-chloronicotinoylchloride.
[0779] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.43-7.46 (1H, m),
7.58 (1H, t, J=7.8 Hz), 7.77 (1H, d, J=7.8 Hz), 7.91-7.95 (2H, m),
8.01 (1H, s), 8.24 (1H, dd, J=2.0, 7.8 Hz), 8.28 (1H, s), 8.36 (1H,
s), 8.41 (1H, s), 8.54-8.56 (1H, m).
Example 15
Preparation of
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)benzamide (Compound No. 7-1733)
##STR00210##
[0780] 15-1
Preparation of
2-chloro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
nitrobenzamide
##STR00211##
[0782] According to the method of 4-3 of Example 4, a target
compound was prepared from
2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline obtained
in 14-1 of Example 14 and 2-chloro-3-nitrobenzoyl chloride.
[0783] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.60 (1H, t, J=7.8
Hz), 7.76 (1H, s), 7.94 (1H, dd, J=1.5, 7.8 Hz), 7.97 (1H, s), 8.03
(1H, dd, J=1.5, 7.8 Hz), 8.39 (1H, s).
15-2
Preparation of
2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
nitrobenzamide
##STR00212##
[0785] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
nitrobenzamide.
[0786] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.51-7.55 (1H, m),
7.97 (1H, s), 8.23 (1H, d, J=12.2 Hz), 8.28-8.32 (1H, m), 8.37 (1H,
s), 8.44-8.48 (1H, m).
15-3
Preparation of
3-amino-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)ph-
enyl)benzamide
##STR00213##
[0788] According to the method of 1-5 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
nitrobenzamide .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H,
broad-s), 7.02-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.52 (1H,
m), 7.94 (1H, s), 8.30-8.35 (2H, m).
15-4
Preparation of
2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
(methylamino)benzamide
##STR00214##
[0790] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)ph-
enyl)benzamide.
[0791] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.95 (3H, s), 4.15
(1H, broad-s), 6.90 (1H, t, J=8.2 Hz), 7.19 (1H, t, J=7.8 Hz), 7.40
(1H, t, J=7.8 Hz), 7.92 (1H, s), 8.30 (1H, s), 8.34 (1H, s).
15-5
Preparation of
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-4-(perfluoropropan-2-yl-
)-6-(trifluoromethyl)phenyl)benzamide (Compound No. 7-1733)
##STR00215##
[0793] According to the method of 1-7 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3--
(methylamino)benzamide and 4-fluorobenzoyl chloride.
[0794] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.50 (3H, s), 6.91
(2H, s), 6.93-7.35 (3H, m), 7.46 (1H, t, J=7.0 Hz), 7.93 (1H, s),
8.01-8.10 (1H, m), 8.13 (1H, broad-s), 8.34 (1H, s).
Example 16
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-N-
-methyl-3-(N-methylbenzamide)benzamide (Compound No. 9-2164)
##STR00216##
[0796] To a solution of 0.100 g (0.150 mmol) of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-
-(N-methylbenzamide)benzamide obtained in 1-7 of Example 1 in 5 ml
of DMF was added 0.00900 g (0.230 mmol) of sodium hydride (60% in
oil), followed by stirring at room temperature for 40 minutes. To
the reaction liquid was added 0.0300 g (0.180 mmol) of methyl
iodide, followed by stirring at the same temperature for 6 hours.
To the reaction liquid were added water and ethyl acetate, and the
organic layer was washed with water and saturated brine, and dried
over anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure and the obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=4:1) to prepare 0.106 g of a target compound
quantitatively.
[0797] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.18-2.19 (3H, m),
3.48 (3H, s), 7.21-7.25 (4H, m), 7.32-7.40 (4H, m), 7.92 (1H, s),
8.13 (1H, s).
Example 17
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
benzamide)-N-methylbenzamide (Compound No. 8-289)
##STR00217##
[0798] 17-1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-nitroben-
zamide
##STR00218##
[0800] According to the method of 4-3 of Example 4, a target
compound was prepared from
2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1 and 3-nitrobenzoyl chloride.
[0801] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.75-7.79 (2H, m),
7.94 (1H, s), 8.17 (1H, d, J=1.0 Hz), 8.28 (1H, dd, J=1.5, 7.8 Hz),
8.48-8.51 (1H, m), 8.76-8.77 (1H, m).
17-2
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N-methyl-3-
-nitrobenzamide
##STR00219##
[0803] According to the method of Example 16, a target compound was
prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-nitroben-
zamide
[0804] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.28 (1/2*3H, s), 3.44
(1/2*3H, s), 7.41 (1/2*1H, t, J=7.8 Hz), 7.71-7.76 (2/2*1H, m),
7.84 (1/2*1H, s), 7.93-7.95 (1/2*1H, m), 7.98 (1/2*1H, s),
8.07-8.09 (2/2*1H, m), 8.14-8.16 (1/2*1H, m), 8.19 (1/2*1H, s),
8.39-8.41 (1/2*1H, m), 8.45-8.46 (1/2*1H, m).
17-3
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N--
methylbenzamide
##STR00220##
[0806] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N-methyl-3-
-nitrobenzamide.
[0807] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.24 (3/4*3H, s), 3.37
(1/4*3H, s), 3.80 (2H, broad-s), 6.47 (1/4*1H, d, J=7.8 Hz),
6.54-6.57 (1/4*1H, m), 6.78-6.84 (5/4*1H, m), 6.86 (3/4*1H, t,
J=2.0 Hz), 6.96 (3/4*1H, d, J=7.8 Hz), 7.23-7.27 (3/4*1H, m), 7.79
(1/4*1H, s), 7.94 (3/4*1H, s), 8.00 (1/4*1H, s), 8.15 (3/4*1H,
s).
17-4
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(4-cyano-
benzamide)-N-methylbenzamide (Compound No. 8-289)
##STR00221##
[0809] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N--
methylbenzamide and 4-cyanobenzoylchloride.
[0810] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.26 (2/3*3H, s), 3.38
(1/3*3H, s), 7.08-7.09 (1/3*1H, 7.12-7.14 (1/3*1H, m), 7.32
(2/3*1H, d, J=7.8 Hz), 7.45-7.49 (3/3*1H, m), 7.72-7.76 (9/3*1H,
m), 7.83 (1/3*1H, s), 7.85-7.89 (4/3*1H, m), 7.95 (2/3*1H, s),
7.98-8.00 (4/3*1H, m), 8.04 (2/3*1H, d, J=6.3 Hz), 8.16 (2/3*1H,
s), 8.57 (2/3*1H, s).
Example 18
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)benza-
mide (Compound No. 6-5913)
##STR00222##
[0811] 18-1
Preparation of 4-(perfluoroethyl)-2-(trifluoromethyl)aniline
##STR00223##
[0813] To 40 ml of an aqueous solution of 7.04 g (40.4 mmol) of 85%
sodium hydrosulfite and 3.40 g (40.4 mmol) of sodium hydrogen
carbonate were added 13.6 g (33.7 mmol) of
2-(trifluoromethyl)aniline and 40 ml of DMF. To this reaction
liquid was added 50 ml of a solution of 11.2 g (45.5 mmol) of
1,1,2,2,2-pentafluoroethyliodide in DMF (DMF was cooled to
-30.degree. C., and 1,1,2,2,2-pentafluoroethyl iodide was dissolved
therein), and placed in an autoclave, followed by stirring at
110.degree. C. for 9 hours. After being left to stand at room
temperature overnight, water and ethyl acetate were added to the
reaction liquid, followed by extraction with ethyl acetate. The
organic layer was washed with water, a saturated aqueous sodium
hydrogen carbonate solution, and saturated brine. The organic layer
was dried over anhydrous sodium sulfate, then the solvent was
evaporated under reduced pressure, and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1.fwdarw.5:1) to prepare 1.95 g (yield 21%)
of a target compound.
[0814] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.53 (2H, broad-s),
6.81 (1H, d, J=8.3 Hz), 7.48 (1H, d, J=8.3 Hz), 7.63 (1H,
broad-s).
18-2
Preparation of
2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)aniline
##STR00224##
[0816] According to the method of 1-2 of Example 1, a target
compound was prepared from
4-(perfluoroethyl)-2-(trifluoromethyl)aniline.
[0817] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.08 (2H, broad-s),
7.62 (1H, s), 7.80 (1H, s).
18-3
Preparation of
N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)-3-nitrobenzamide
##STR00225##
[0819] To a solution of 2.50 g (6.99 mmol) of
2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)aniline in 20 ml of
pyridine was added 2.72 g (14.7 mmol) of 3-nitrobenzoyl chloride,
followed by stirring at 100.degree. C. for 12 hours. To the
reaction liquid were added water and ethyl acetate, followed by
extraction with ethyl acetate. The organic layer was washed with 1
M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate
solution, and saturated brine. The organic layer was dried over
anhydrous sodium sulfate, and then the solvent was evaporated under
reduced pressure. To the obtained residue were added THF and an
aqueous sodium hydroxide solution, followed by stirring at room
temperature for 8 hours. The reaction liquid was extracted/dried in
the same manner as described above, and the solvent was evaporated
under reduced pressure. The obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=7:1.fwdarw.5:1) to prepare 0.202 g (yield 6%) of a target
compound.
[0820] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.75 (1H, s), 7.78
(1H, t, J=7.8 Hz), 7.94 (1H, s), 8.17 (1H, s), 8.29-8.30 (1H, m),
8.50-8.52 (1H, m), 8.78 (1H, t, J=2.0 Hz).
18-4
Preparation of
3-amino-N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)benzamide
##STR00226##
[0822] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)-3-nitrobenzamide-
.
[0823] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.89 (2H, broad-s),
6.90-6.92 (1H, m), 7.23-7.32 (3H, m), 7.64 (1H, s), 7.90 (1H, s),
8.13 (1H, s).
18-5
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)benza-
mide (Compound No. 6-5913)
##STR00227##
[0825] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)phenyl)benzamide
[0826] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.51-7.62 (4H, m),
7.72 (1H, dd, J=1.5, 7.8 Hz), 7.89-8.00 (6H, m), 8.14 (1H, s), 8.27
(1H, t, J=2.0 Hz).
Example 19
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-4-cyanobenzamide (Compound No. 1-627)
##STR00228##
[0827] 19-1
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-
-nitrobenzamide
##STR00229##
[0829] According to the method of 4-3 of Example 4, a target
compound was prepared from 4-fluoro-3-nitrobenzoyl chloride
prepared from 4-fluoro-3-nitrobenzoic acid and thionyl chloride,
and 2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)aniline
obtained in 1-2 of Example 1.
[0830] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.47-7.50 (1H, m),
7.92 (2H, d, J=5.9 Hz), 8.16 (1H, s), 8.23-8.28 (1H, m), 8.65-8.67
(1H, m).
19-2
Preparation of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3--
nitrobenzamide
##STR00230##
[0832] To a solution of 0.500 g (0.870 mmol) of
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-
-nitrobenzamide in 5 ml of DMF was added 0.0639 g (1.31 mmol) of
sodium cyanide, followed by stirring at room temperature for 10
hours. To the reaction liquid were added water and ethyl acetate,
followed by extraction with ethyl acetate. The organic layer was
washed with a 10% aqueous sodium hydroxide solution and saturated
brine. The organic layer was dried over anhydrous sodium sulfate,
and then the solvent was evaporated under reduced pressure. The
obtained residue was purified by silica gel column chromatography
to prepare 0.0500 g (yield 10%) of a target compound.
[0833] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.80 (1H, s), 7.96
(1H, s), 8.12-8.14 (1H, m), 8.18 (1H, s), 8.36 (1H, dd, J=2.0, 8.3
Hz), 8.84 (1H, d, J=1.5 Hz).
19-3
Preparation of
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
cyanobenzamide
##STR00231##
[0835] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-cyano-3--
nitrobenzamide
[0836] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.68 (2H, broad-s),
7.18 (1H, dd, J=1.9, 8.3 Hz), 7.29 (1H, s), 7.52-7.55 (1H, m), 7.68
(1H, s), 7.92 (1H, s), 8.14 (1H, d, J=1.5 Hz).
19-4
Preparation of
3-benzamide-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl-
)-4-cyanobenzamide (Compound No. 1-627)
##STR00232##
[0838] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4--
cyanobenzamide.
[0839] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.56-7.59 (3H, m),
7.64-7.66 (1H, m), 7.80-7.87 (2H, m), 7.94-7.97 (2H, m), 8.16 (1H,
s), 8.46 (1H, s), 8.57 (1H, s), 9.16 (1H, s).
[0840] Next, Preparation Examples in which the compound of the
present invention is contained as an active ingredient will be
shown, but the present invention is not limited thereto. Further,
in Preparation Examples, parts represent parts by weight.
Preparation Example 1
[0841] 20 parts of the compound represented by Formula (1) of the
present invention, 10 parts of polyoxyethylene styrylphenyl ether,
and 70 parts of xylene were mixed uniformly to obtain an
emulsion.
Preparation Example 2
[0842] 10 parts of the compound represented by Formula (1) of the
present invention, 2 parts of sodium lauryl sulfate, 2 parts of
dialkyl sulfosuccinate, 1 part of a (3-naphthalene sulfonic acid
formalin condensate sodium salt, and 85 parts of diatomaceous earth
were stirred and mixed uniformly to obtain a wettable powder.
Preparation Example 3
[0843] 0.3 parts of the compound represented by Formula (1) of the
present invention and 0.3 parts of white carbon were mixed
uniformly, and 99.2 parts of clay and 0.2 parts of DRILESS A
(manufactured by Sankyo Agro Co., Ltd.) were added thereto,
followed by pulverizing and mixing uniformly, thereby obtaining
powders.
Preparation Example 4
[0844] 3 parts of the compound represented by Formula (1) of the
present invention, 1.5 parts of a polyoxyethylene/polyoxypropylene
condensate, 3 parts of carboxymethyl cellulose, 64.8 parts of clay,
and 27.7 parts of talc were pulverized and mixed uniformly, and
water was added thereto, followed by kneading, granulating, and
drying, thereby obtaining powders.
Preparation Example 5
[0845] 10 parts of the compound represented by Formula (1) of the
present invention, 3 parts of a .beta.-naphthalene sulfonic acid
formalin condensate sodium salt, 1 part of tristyrylphenol, 5 parts
of propylene glycol, 0.5 parts of a silicon-based defoaming agent,
and 33.5 parts of water were sufficiently stirred and mixed, and
then 0.3 parts of xanthan gum and 46.7 parts of water were mixed
therewith, followed by stirring and mixing again, thereby obtaining
a flowable Formulation.
Preparation Example 6
[0846] 20 parts of the compound represented by Formula (1) of the
present invention, 6 parts of a naphthalene sulfonic acid
formaldehyde condensate metal salt, 1 part of dialkylsulfosuccinate
metal salt, and 73 parts of calcium carbonate were pulverized and
mixed uniformly, and water was added thereto, followed by kneading,
granulating, and drying, thereby obtaining a granule wettable
powder.
[0847] For the use of Formulations obtained above, Formulation was
diluted to 1-fold to 10000-fold with water or was not diluted, and
then directly sprayed.
[0848] Next, the usefulness of the compound of the present
invention as a pest control agent will be described specifically
with reference to the following Test Examples, but the present
invention is not limited thereto.
Test Example 1
[0849] Pesticidal Test against Spodoptera litura
[0850] A piece of a cabbage leaf was immersed for 30 seconds in a
chemical solution in which a test compound had been prepared at a
predetermined concentration, and air-dried, and then put into a 7
cm polyethylene cup having a filter paper laid on the bottom
thereof, and 2-stage larvae of Spodoptera litura were released.
They were left to stand in a thermostatic chamber at 25.degree. C.,
and the numbers of the living pests and the dead pests were
examined after 6 days. The test was carried out with five larvae
per group in two replicates.
[0851] Further, the following compound (A) disclosed in the
pamphlet of International Publication WO 2005/073165 was used as a
comparative compound.
##STR00233##
[0852] As the results of the above tests, the compounds of Compound
Nos. 1-470, 1-491, 1-513, 1-627, 1-1925, 2-491, 6-38, 6-39, 6-45,
6-46, 6-47, 6-57, 6-60, 6-71, 6-72, 6-78, 6-79, 6-80, 6-90, 6-93,
6-111, 6-147, 6-268, 6-269, 6-270, 6-271, 6-272, 6-288, 6-289,
6-290, 6-293, 6-300, 6-304, 6-306, 6-311, 6-346, 6-347, 6-348,
6-349, 6-366, 6-367, 6-368, 6-382, 6-389, 6-424, 6-425, 6-426,
6-427, 6-428, 6-444, 6-445, 6-446, 6-448, 6-449, 6-450, 6-452,
6-453, 6-460, 6-461, 6-467, 6-502, 6-503, 6-504, 6-505, 6-522,
6-523, 6-524, 6-538, 6-545, 6-804, 6-824, 6-825, 6-840, 6-1104,
6-1105, 6-1106, 6-1107, 6-1124, 6-1125, 6-1126, 6-1140, 6-1147,
6-1182, 6-1183, 6-1184, 6-1185, 6-1202, 6-1203, 6-1204, 6-1218,
6-1225, 6-1260, 6-1261, 6-1262, 6-1263, 6-1280, 6-1281, 6-1282,
6-1296, 6-1303, 6-1338, 6-1339, 6-1340, 6-1341, 6-1358, 6-1359,
6-1360, 6-1374, 6-1381, 6-1574, 6-1575, 6-1576, 6-1577, 6-1594,
6-1595, 6-1596, 6-1610, 6-1617, 6-1652, 6-1653, 6-1654, 6-1655,
6-1672, 6-1673, 6-1674, 6-1688, 6-1695, 6-1730, 6-1731, 6-1732,
6-1733, 6-1734, 6-1750, 6-1751, 6-1752, 6-1754, 6-1755, 6-1766,
6-1773, 6-1808, 6-1809, 6-1810, 6-1811, 6-1828, 6-1829, 6-1830,
6-1851, 6-2110, 6-3348, 6-3384, 6-5902, 6-5903, 6-5904, 6-5905,
6-5906, 6-5907, 6-5908, 6-5909, 6-5910, 6-5911, 6-5912, 7-38, 7-39,
7-45, 7-46, 7-47, 7-57, 7-60, 7-71, 7-72, 7-78, 7-79, 7-80, 7-90,
7-93, 7-132, 7-147, 7-268, 7-269, 7-270, 7-271, 7-285, 7-286,
7-288, 7-289, 7-290, 7-299, 7-300, 7-301, 7-303, 7-304, 7-305,
7-311, 7-346, 7-347, 7-348, 7-349, 7-366, 7-367, 7-368, 7-382,
7-389, 7-424, 7-425, 7-426, 7-427, 7-428, 7-444, 7-445, 7-446,
7-449, 7-460, 7-467, 7-502, 7-504, 7-505, 7-522, 7-523, 7-538,
7-804, 7-824, 7-825, 7-840, 7-948, 7-969, 7-984, 7-1104, 7-1105,
7-1106, 7-1107, 7-1124, 7-1125, 7-1126, 7-1140, 7-1147, 7-1182,
7-1183, 7-1184, 7-1185, 7-1202, 7-1203, 7-1204, 7-1218, 7-1225,
7-1260, 7-1261, 7-1262, 7-1263, 7-1280, 7-1281, 7-1282, 7-1296,
7-1303, 7-1338, 7-1339, 7-1340, 7-1341, 7-1358, 7-1359, 7-1360,
7-1374, 7-1381, 7-1417, 7-1574, 7-1575, 7-1576, 7-1577, 7-1594,
7-1595, 7-1596, 7-1605, 7-1606, 7-1608, 7-1610, 7-1616, 7-1617,
7-1638, 7-1639, 7-1645, 7-1652, 7-1672, 7-1673, 7-1730, 7-1731,
7-1732, 7-1733, 7-1750, 7-1751, 7-1752, 7-1764, 7-1766, 7-1773,
7-1794, 7-1808, 7-1809, 7-1810, 7-1811, 7-1828, 7-1829, 7-1844,
7-1851, 7-3348, 7-3369, 7-3384, 7-5902, 7-5903, 7-5904, 7-5905,
7-5906, 7-5907, 7-5910, 8-268, 8-288, 8-289, 8-304, 8-804, 8-824,
8-840, 9-270, 9-290, 9-291, 9-306, 9-2164, 9-2322, 11-777, 11-835,
12-777, 12-835, 12-864, 27-627, and 27-663 each showed a pesticidal
rate of 70% or more at a concentration of 1 ppm.
[0853] Furthermore, the compounds of Compound Nos. 1-506, 1-1968,
2-513, 2-518, 6-454, 6-5913, 6-5914, 7-316, 7-5911, 7-5912, 7-5908,
7-5909, 17-1103, and 27-628 each showed a pesticidal rate of 70% or
more at a concentration of 10 ppm.
[0854] Meanwhile, the compound (A) had a pesticidal rate of 50% or
less at a concentration of 10 ppm.
Test Example 2
[0855] Pesticidal Test against Plutella xylostella
[0856] A piece of a cabbage leaf was immersed for 30 seconds in a
chemical solution in which a test compound had been prepared at a
predetermined concentration, and air-dried, and then put into a 7
cm polyethylene cup having a filter paper laid on the bottom
thereof, and 2-stage larvae of Plutella xylostella were released.
They were left to stand in a thermostatic chamber at 25.degree. C.,
and the numbers of the living pests and the dead pests were
examined after 6 days. The test was carried out with five larvae
per group in two replicates.
[0857] Further, the above compound (A) was used as a comparative
compound.
[0858] As the results of the above tests, the compounds of Compound
Nos. 1-491, 1-513, 1-627, 1-1925, 1-1968, 2-491, 2-513, 6-38, 6-39,
6-45, 6-46, 6-47, 6-57, 6-71, 6-72, 6-78, 6-79, 6-80, 6-90, 6-111,
6-147, 6-268, 6-270, 6-271, 6-272, 6-288, 6-289, 6-290, 6-293,
6-300, 6-304, 6-306, 6-346, 6-347, 6-348, 6-349, 6-366, 6-367,
6-368, 6-382, 6-389, 6-424, 6-425, 6-426, 6-427, 6-428, 6-444,
6-445, 6-446, 6-449, 6-450, 6-453, 6-460, 6-461, 6-467, 6-502,
6-503, 6-504, 6-505, 6-522, 6-523, 6-524, 6-538, 6-545, 6-804,
6-824, 6-825, 6-840, 6-1104, 6-1105, 6-1106, 6-1107, 6-1124,
6-1125, 6-1126, 6-1140, 6-1147, 6-1182, 6-1183, 6-1184, 6-1185,
6-1202, 6-1203, 6-1204, 6-1218, 6-1225, 6-1260, 6-1261, 6-1262,
6-1263, 6-1280, 6-1281, 6-1282, 6-1296, 6-1303, 6-1338, 6-1339,
6-1340, 6-1341, 6-1358, 6-1359, 6-1360, 6-1374, 6-1381, 6-1574,
6-1575, 6-1576, 6-1577, 6-1594, 6-1595, 6-1596, 6-1610, 6-1617,
6-1652, 6-1653, 6-1654, 6-1655, 6-1672, 6-1673, 6-1674, 6-1688,
6-1695, 6-1730, 6-1731, 6-1732, 6-1733, 6-1734, 6-1750, 6-1751,
6-1752, 6-1754, 6-1755, 6-1766, 6-1773, 6-1808, 6-1809, 6-1810,
6-1811, 6-1828, 6-1829, 6-1830, 6-1851, 6-2110, 6-3348, 6-3384,
6-5903, 6-5904, 6-5905, 6-5906, 6-5907, 6-5908, 6-5909, 6-5910,
6-5911, 6-5912, 7-38, 7-39, 7-45, 7-46, 7-47, 7-57, 7-60, 7-71,
7-72, 7-78, 7-79, 7-80, 7-90, 7-93, 7-132, 7-147, 7-268, 7-271,
7-286, 7-288, 7-289, 7-290, 7-299, 7-300, 7-301, 7-303, 7-304,
7-305, 7-311, 7-346, 7-347, 7-348, 7-349, 7-366, 7-367, 7-368,
7-382, 7-389, 7-424, 7-425, 7-426, 7-427, 7-428, 7-444, 7-445,
7-446, 7-449, 7-460, 7-467, 7-502, 7-504, 7-505, 7-522, 7-523,
7-538, 7-824, 7-840, 7-948, 7-969, 7-984, 7-1104, 7-1105, 7-1106,
7-1107, 7-1124, 7-1125, 7-1126, 7-1140, 7-1147, 7-1182, 7-1183,
7-1184, 7-1185, 7-1202, 7-1203, 7-1204, 7-1218, 7-1225, 7-1260,
7-1261, 7-1262, 7-1263, 7-1280, 7-1281, 7-1282, 7-1296, 7-1303,
7-1338, 7-1339, 7-1340, 7-1341, 7-1358, 7-1359, 7-1360, 7-1374,
7-1381, 7-1417, 7-1574, 7-1575, 7-1576, 7-1577, 7-1594, 7-1595,
7-1596, 7-1605, 7-1606, 7-1608, 7-1610, 7-1616, 7-1617, 7-1638,
7-1639, 7-1645, 7-1652, 7-1672, 7-1673, 7-1730, 7-1731, 7-1732,
7-1733, 7-1750, 7-1751, 7-1752, 7-1764, 7-1766, 7-1773, 7-1794,
7-1808, 7-1809, 7-1810, 7-1811, 7-1828, 7-1829, 7-1844, 7-1851,
7-3348, 7-3369, 7-3384, 7-5902, 7-5903, 7-5904, 7-5905, 7-5906,
7-5907, 7-5909, 7-5910, 8-268, 8-288, 8-289, 8-304, 8-824, 9-270,
9-290, 9-291, 9-306, 9-2164, 9-2322, 11-777, 11-835, 12-777,
12-835, and 12-864 each showed a pesticidal rate of 70% or more at
a concentration of 1 ppm.
[0859] Furthermore, the compounds of Compound Nos. 1-470, 1-506,
2-518, 6-60, 6-93, 6-269, 6-311, 6-448, 6-452, 6-454, 6-5913,
6-5914, 7-269, 7-270, 7-285, 7-316, 7-804, 7-825, 7-5908, 7-5911,
7-5912, 8-804, 8-840, 17-1103, 27-627, 27-628, and 27-663 each
showed a pesticidal rate of 70% or more at a concentration of 10
ppm.
[0860] Meanwhile, the compound (A) had a pesticidal rate of 50% or
less at a concentration of 10 ppm.
Test Example 3
[0861] Pesticidal Test against Adoxophyes honmai
[0862] A thinly sliced artificial feed was immersed for 30 seconds
in a chemical solution in which a test compound had been prepared
at a predetermined concentration, and air-dried, and then put into
a 7 cm polyethylene cup having a filter paper laid on the bottom
thereof, and 2-stage larvae of Adoxophyes honmai were released.
They were left to stand in a thermostatic chamber at 25.degree. C.,
and the numbers of the living pests and the dead pests were
examined after 6 days. The test was carried out with five larvae
per group in two replicates.
[0863] Further, the above compound (A) was used as a comparative
compound.
[0864] As the results of the above tests, the compounds of Compound
Nos. 6-72, 6-80, 6-90, 6-347, 6-348, 6-349, 6-366, 6-382, 6-427,
6-446, 6-449, 6-460, 6-503, 6-504, 6-505, 6-522, 6-524, 6-538,
6-1106, 6-1182, 6-1202, 6-1260, 6-1262, 6-1263, 6-1341, 6-1358,
6-1574, 6-1576, 6-1594, 6-1596, 6-1652, 6-1654, 6-1655, 6-1672,
6-1674, 6-1688, 6-1730, 6-1732, 6-1733, 6-1750, 6-1809, 6-1811,
6-1828, 6-1830, 7-348, 7-366, 7-382, 7-502, 7-505, 7-522, 7-538,
7-1106, 7-1202, 7-1262, 7-1280, 7-1303, 7-1338, 7-1358, 7-1574,
7-1576, 7-1594, 7-1605, 7-1652, 7-1730, 7-1732, 7-1733, 7-1750,
7-1764, 7-1808, 7-1809, 7-1810, and 7-1811 each showed a pesticidal
rate of 70% or more at a concentration of 1 ppm.
[0865] Furthermore, the compounds of Compound Nos. 6-271, 6-367,
6-389, 6-426, 6-523, 6-1104, 6-1577, 6-1695, 6-1851, 6-2110, 7-424,
7-444, 7-523, 7-1104, 7-1124, 7-1260, 7-1263, 7-1577, 7-1616,
7-1731, 7-1773, and 7-1851 each showed a pesticidal rate of 70% or
more at a concentration of 10 ppm.
[0866] Meanwhile, the compound (A) had a pesticidal rate of 50% or
less at a concentration of 10 ppm.
Test Example 4
[0867] Pesticidal Test against Choristoneura magnanima
[0868] A thinly sliced artificial feed was immersed for 30 seconds
in a chemical solution in which a test compound had been prepared
at a predetermined concentration, and air-dried, and then put into
a 7 cm polyethylene cup having a filter paper laid on the bottom
thereof, and 2-stage larvae of Choristoneura magnanima were
released. They were left to stand in a thermostatic chamber at
25.degree. C., and the numbers of the living pests and the dead
pests were examined after 6 days. The test was carried out with
five larvae per group in two replicates.
[0869] Further, the above compound (A) was used as a comparative
compound.
[0870] As the results of the above tests, the compounds of Compound
Nos. 6-72, 6-80, 6-90, 6-271, 6-349, 6-366, 6-367, 6-426, 6-427,
6-1104, 6-1106, 6-1182, 6-1260, 6-1263, 6-1358, 6-1574, 6-1577,
6-1595, 6-1596, 6-1652, 6-1654, 6-1655, 6-1672, 6-1673, 6-1674,
6-1695, 6-1730, 6-1732, 6-1733, 6-1750, 6-1751, 6-1809, 6-1811,
6-1828, 6-1829, 6-1830, 6-1851, 7-90, 7-348, 7-366, 7-382, 7-389,
7-444, 7-502, 7-504, 7-505, 7-523, 7-1104, 7-1106, 7-1107, 7-1124,
7-1125, 7-1260, 7-1262, 7-1263, 7-1280, 7-1281, 7-1303, 7-1358,
7-1359, 7-1574, 7-1576, 7-1577, 7-1594, 7-1595, 7-1605, 7-1616,
7-1617, 7-1652, 7-1730, 7-1732, 7-1733, 7-1750, 7-1764, 7-1773,
7-1808, 7-1809, 7-1810, 7-1811, 7-1829, and 7-1851 each showed a
pesticidal rate of 70% or more at a concentration of 1 ppm.
[0871] Furthermore, the compounds of Compound Nos. 6-382, 6-446,
6-460, 6-2110, 7-424, 7-538, and 7-1606 each showed a pesticidal
rate of 70% or more at a concentration of 10 ppm.
[0872] Meanwhile, the compound (A) had a pesticidal rate of 50% or
less at a concentration of 10 ppm.
Test Example 5
[0873] Pesticidal Test against Helicoverpa armigera
[0874] A cabbage leaf disk was immersed for 30 seconds in a
chemical solution in which a test compound had been prepared at a
predetermined concentration, and air-dried. The leaf disk was put
into a 6-hole plastic cup having a filter paper laid on the bottom
thereof, and 2-stage larvae of Helicoverpa armigera were released
with one insect being released per hole. They were left to stand in
a thermostatic chamber at 25.degree. C., and the numbers of the
living pests and the dead pests were examined after 3 days. The
test was carried out with five larvae per group in two
replicates.
[0875] Further, the above compound (A) was used as a comparative
compound.
[0876] As the results of the above tests, the compounds of Compound
Nos. 6-72, 6-80, 6-90, 6-271, 6-347, 6-348, 6-349, 6-366, 6-367,
6-382, 6-389, 6-426, 6-427, 6-446, 6-449, 6-460, 6-503, 6-504,
6-505, 6-522, 6-523, 6-524, 6-538, 6-1104, 6-1106, 6-1260, 6-1262,
6-1263, 6-1281, 6-1341, 6-1358, 6-1359, 6-1574, 6-1576, 6-1577,
6-1594, 6-1595, 6-1596, 6-1652, 6-1654, 6-1655, 6-1672, 6-1673,
6-1674, 6-1695, 6-1730, 6-1732, 6-1733, 6-1750, 6-1751, 6-1808,
6-1809, 6-1811, 6-1828, 6-1829, 6-1830, 6-1851, 6-2110, 7-90,
7-348, 7-366, 7-382, 7-389, 7-424, 7-444, 7-502, 7-505, 7-522,
7-523, 7-538, 7-1106, 7-1107, 7-1125, 7-1262, 7-1263, 7-1280,
7-1303, 7-1338, 7-1358, 7-1359, 7-1574, 7-1576, 7-1577, 7-1594,
7-1595, 7-1605, 7-1606, 7-1616, 7-1617, 7-1652, 7-1730, 7-1731,
7-1732, 7-1733, 7-1750, 7-1751, 7-1764, 7-1773, 7-1808, 7-1809,
7-1810, 7-1811, 7-1829, and 7-1851 each showed a pesticidal rate of
70% or more at a concentration of 1 ppm.
[0877] Furthermore, the compound of Compound No. 7-1104 showed a
pesticidal rate of 70% or more at a concentration of 10 ppm.
[0878] Meanwhile, the compound (A) had a pesticidal rate of 50% or
less at a concentration of 10 ppm.
Test Example 6
[0879] Pesticidal Test against Laodelphax striatellus
[0880] 2.5 ml of an acetone solution in which a test compound had
been prepared at a predetermined concentration was sprayed on rice
seedlings, air-dried, and then put into a glass tube having a
diameter of 3 cm and a height of 13 cm, having water therein, and
3-stage larvae of Laodelphax striatellus were released and the tube
was capped. They were left to stand in a thermostatic chamber at
25.degree. C., and the numbers of the living pests and the dead
pests were examined after 6 days. The test was carried out with ten
larvae per group in two replicates.
[0881] As the results of the above tests, the compounds of Compound
Nos. 1-491, 1-627, 2-491, 6-39, 6-45, 6-47, 6-57, 6-71, 6-72, 6-79,
6-80, 6-90, 6-147, 6-268, 6-269, 6-270, 6-271, 6-290, 6-304, 6-306,
6-311, 6-346, 6-347, 6-368, 6-382, 6-425, 6-427, 6-444, 6-445,
6-446, 6-460, 6-461, 6-503, 6-1104, 6-1106, 6-1107, 6-1124, 6-1126,
6-1140, 6-1147, 6-1182, 6-1183, 6-1184, 6-1185, 6-1202, 6-1203,
6-1204, 6-1218, 6-1225, 6-1260, 6-1261, 6-1262, 6-1263, 6-1280,
6-1281, 6-1282, 6-1296, 6-1303, 6-1338, 6-1339, 6-1340, 6-1341,
6-1358, 6-1359, 6-1360, 6-1374, 6-1381, 6-1574, 6-1575, 6-1576,
6-1577, 6-1594, 6-1595, 6-1596, 6-1610, 6-1617, 6-1652, 6-1653,
6-1654, 6-1655, 6-1672, 6-1673, 6-1674, 6-1688, 6-1695, 6-1730,
6-1731, 6-1732, 6-1733, 6-1734, 6-1750, 6-1751, 6-1752, 6-1754,
6-1766, 6-1773, 6-1808, 6-1809, 6-1810, 6-1811, 6-1828, 6-1829,
6-1830, 6-1851, 6-2110, 6-3348, 6-3384, 6-5903, 6-5904, 6-5905,
6-5906, 6-5907, 6-5908, 6-5909, 6-5910, 6-5911, 6-5914, 7-47, 7-57,
7-90, 7-268, 7-285, 7-286, 7-288, 7-289, 7-301, 7-303, 7-304,
7-305, 7-311, 7-316, 7-346, 7-348, 7-368, 7-382, 7-389, 7-424,
7-426, 7-427, 7-444, 7-445, 7-446, 7-460, 7-467, 7-538, 7-825,
7-840, 7-948, 7-984, 7-1104, 7-1105, 7-1106, 7-1107, 7-1124,
7-1125, 7-1126, 7-1140, 7-1147, 7-1182, 7-1183, 7-1184, 7-1185,
7-1202, 7-1203, 7-1204, 7-1218, 7-1225, 7-1260, 7-1261, 7-1262,
7-1263, 7-1280, 7-1281, 7-1282, 7-1296, 7-1303, 7-1338, 7-1339,
7-1340, 7-1341, 7-1358, 7-1359, 7-1360, 7-1374, 7-1381, 7-1417,
7-1574, 7-1575, 7-1576, 7-1577, 7-1594, 7-1595, 7-1596, 7-1605,
7-1606, 7-1608, 7-1610, 7-1616, 7-1617, 7-1638, 7-1639, 7-1645,
7-1652, 7-1672, 7-1673, 7-1730, 7-1731, 7-1732, 7-1733, 7-1750,
7-1751, 7-1752, 7-1764, 7-1766, 7-1773, 7-1794, 7-1808, 7-1809,
7-1810, 7-1811, 7-1828, 7-1829, 7-1844, 7-1851, 7-3348, 7-3369,
7-5902, 7-5903, 7-5904, 7-5906, 7-5907, 7-5909, 7-5912, 8-289,
8-304, 8-840, 9-270, 9-290, 9-291, 9-306, 9-2164, 9-2322, 12-835,
and 12-864 each showed a pesticidal rate of 70% or more at a
concentration of 100 ppm.
Test Example 7
[0882] Pesticidal Test against Musca domestica
[0883] 1 ml of an acetone solution in which a test compound had
been prepared at a predetermined concentration was added dropwise
to a petri dish having a diameter of 9 cm, and air-dried, and then
the female adults of Musca domestica were released and the petri
dish was capped. They were left to stand in a thermostatic chamber
at 25.degree. C., and the numbers of the living pests and the dead
pests were examined after 1 day. The test was carried out with five
larvae per group in two replicates.
[0884] As the results of the above tests, the compounds of Compound
Nos. 1-1925, 1-1968, 6-39, 6-47, 6-72, 6-272, 6-293, 6-346, 6-347,
6-348, 6-366, 6-368, 6-382, 6-389, 6-426, 6-427, 6-428, 6-450,
6-452, 6-453, 6-460, 6-503, 6-504, 6-505, 6-522, 6-523, 6-524,
6-538, 6-1105, 6-1107, 6-1124, 6-1125, 6-1126, 6-1147, 6-1184,
6-1204, 6-1218, 6-1260, 6-1281, 6-1338, 6-1341, 6-1358, 6-1359,
6-1360, 6-1374, 6-1575, 6-1576, 6-1577, 6-1594, 6-1596, 6-1617,
6-1652, 6-1672, 6-1673, 6-1695, 6-1730, 6-1731, 6-1732, 6-1733,
6-1734, 6-1750, 6-1751, 6-1752, 6-1773, 6-1808, 6-1809, 6-1810,
6-1811, 6-1828, 6-1829, 6-1830, 6-1851, 6-2110, 6-5905, 7-39, 7-57,
7-90, 7-268, 7-346, 7-348, 7-349, 7-366, 7-367, 7-368, 7-382,
7-389, 7-424, 7-428, 7-444, 7-446, 7-449, 7-504, 7-522, 7-538,
7-1104, 7-1105, 7-1106, 7-1107, 7-1126, 7-1262, 7-1280, 7-1282,
7-1296, 7-1303, 7-1338, 7-1340, 7-1358, 7-1359, 7-1360, 7-1381,
7-1417, 7-1574, 7-1575, 7-1576, 7-1577, 7-1596, 7-1652, 7-1731,
7-1732, 7-1733, 7-1750, 7-1752, 7-1764, 7-1766, 7-1730, 7-1773,
7-1794, 7-1808, 7-1809, 7-1810, 7-1811, 7-1828, 7-1829, 7-1851,
9-2164, 9-2322, 11-777, 11-835, 12-777, 12-835, 12-864, 17-1103,
and 27-627 each showed a pesticidal rate of 70% or more at a
concentration of 100 ppm.
Test Example 8
[0885] Pesticidal Test against Blattella germanica
[0886] 1 ml of an acetone solution in which a test compound had
been prepared at a predetermined concentration was added dropwise
to a petri dish having a diameter of 9 cm, and air-dried, and then
the female adults of Blattella germanica were released and the
petri dish was capped. They were left to stand in a thermostatic
chamber at 25.degree. C., and the numbers of the living pests and
the dead pests were examined after 1 day. The test was carried out
with five larvae per group in two replicates.
[0887] As the results of the above tests, the compounds of Compound
Nos. 1-1925, 6-39, 6-47, 6-346, 6-347, 6-367, 6-368, 6-382, 6-389,
6-426, 6-427, 6-503, 6-538, 6-1105, 6-1106, 6-1107, 6-1124, 6-1125,
6-1126, 6-1147, 6-1184, 6-1204, 6-1218, 6-1280, 6-1296, 6-1338,
6-1358, 6-1359, 6-1575, 6-1576, 6-1577, 6-1594, 6-1595, 6-1596,
6-1610, 6-1617, 6-1730, 6-1731, 6-1732, 6-1733, 6-1750, 6-1751,
6-1752, 6-1773, 6-1811, 6-5905, 7-57, 7-268, 7-305, 7-347, 7-349,
7-367, 7-382, 7-389, 7-424, 7-444, 7-446, 7-502, 7-505, 7-538,
7-1104, 7-1105, 7-1106, 7-1107, 7-1125, 7-1126, 7-1261, 7-1262,
7-1280, 7-1282, 7-1296, 7-1303, 7-1381, 7-1574, 7-1575, 7-1576,
7-1577, 7-1594, 7-1595, 7-1596, 7-1617, 7-1731, 7-1732, 7-1733,
7-1750, 7-1752, 7-1766, 7-1773, and 7-1851 each showed a pesticidal
rate of 70% or more at a concentration of 100 ppm.
Test Example 9
[0888] Pesticidal Test against Culex pipiens molestus
[0889] 1 ml of an acetone solution in which a test compound had
been prepared at a predetermined concentration was added dropwise
to a petri dish having a diameter of 9 cm, and air-dried, and then
the female adults of Culex pipiens molestus were released and the
petri dish was capped. They were left to stand in a thermostatic
chamber at 25.degree. C., and the numbers of the living pests and
the dead pests were examined after 1 day of treatment. The test was
carried out with five larvae per group in two replicates.
[0890] As the results of the above tests, the compounds of Compound
Nos. Compound No. 7-424, 7-1574, 7-1577, 7-1730, 7-1732, and 7-1733
each showed a pesticidal rate of 70% or more at a concentration of
1000 ppm.
Test Example 10
[0891] Pesticidal Test against Coptotermes formosanus
[0892] 20 .mu.l of an acetone solution in which a test compound had
been prepared at a predetermined concentration was added dropwise
to the filter paper having a diameter of 2.6 mm included in a
polypropylene cup, and air-dried, and then 20 .mu.l of water was
added thereto. Coptotermes formosanus was released and the cup was
capped. They were left to stand in a thermostatic chamber at
28.degree. C., and the numbers of the living pests and the dead
pests were examined after 5 days of treatment. The test was carried
out with ten larvae per group in two replicates.
[0893] As the results of the above tests, the compounds of Compound
Nos. Compound No. 6-460, 6-1260, 6-1652, 7-268, 7-424, 7-1104,
7-1574, 7-1577, 7-1730, 7-1732, and 7-1733 each showed a pesticidal
rate of 70% or more at a concentration of 30 ppm.
[0894] According to the present invention, it becomes possible to
provide a novel amide derivative. The amide derivative shows a
significant effect for a pest control activity, and has a high
industrial availability.
[0895] The present invention also provides a composition and method
for exterminating animal parasites.
[0896] WO2005/21488, WO2005/73165, WO2006/137376, and WO2006/137395
disclose various compounds which are amide derivatives having the
ability to control pests, and methods for using them. Further
WO2009/080203 discloses amide derivatives which are animal
parasiticides, and methods for using them.
[0897] In addition, conventional parasiticides for administration
to an animal to exterminate animal parasites include formulations
of imidacloprid, fipronil, etc.
[0898] However, some parasites are impossible or difficult to
exterminate with said animal parasiticides.
[0899] Thus, an objective of the invention is to provide a
composition that has excellent activity for exterminating animal
parasites, and a method for exterminating animal parasites.
[0900] As the result of earnest research for solving the above
problem, the present inventors found that an aromatic carboxamide
derivative represented by Formula (A1) of the present invention is
a novel compound that is not disclosed in the literature, and a
composition containing the present aromatic carboxamide derivative
as an active ingredient has excellent activity for exterminating
animal parasites, thereby completing the present invention.
[0901] A first aspect of the present invention provides a
composition for exterminating animal parasites which comprises as
an active ingredient at least one amide derivative represented by
the following Formula (A1).
##STR00234##
[0902] In Formula (A1), Q.sub.1 represents a phenyl group or a
phenyl group substituted with a halogen atom; X.sub.1 represents a
fluorine atom, and X.sub.2, X.sub.3, and X.sub.4 are each a
hydrogen atom; R.sub.1 represents a hydrogen atom or a C1-C3 alkyl
group; R.sub.2 is a hydrogen atom; Y.sub.1 and Y.sub.5 each
independently represent a halogen atom or a C1-C3 haloalkyl group;
Y.sub.2 and Y.sub.4 each represent a hydrogen atom; and Y.sub.3
represents a heptafluoroisopropyl group.
[0903] In Formula (A1), Q.sub.1 represents a phenyl group or a
phenyl group substituted with a single fluorine atom; R.sub.1
represents a hydrogen atom or a methyl group; and Y.sub.1 and
Y.sub.5 each independently represent a bromine or iodine atom or a
trifluoromethyl group preferably.
[0904] The amide derivative represented by Formula (A1) is
preferably
2-fluoro-3-(N-methylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluor-
opropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamide)-N-(2-iodo-6-trifluoromethyl-4-(he-
ptafluoropropan-2-yl)phenyl)benzamide,
2-fluoro-3-(4-fluorobenzamide)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoro-
propan-2-yl)phenyl)benzamide, or
2-fluoro-3-(N-methylbenzamide)-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)p-
henyl)benzamide.
[0905] In Formula (A1), Q.sub.1 represents preferably a phenyl
group, a 2-fluorophenyl group, a 3-fluorophenyl group, a
4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl
group, a 4-chlorophenyl group, a 2-bromophenyl group, a
3-bromophenyl group, a 4-bromophenyl group, a 2-iodophenyl group, a
3-iodophenyl group, or a 4-iodophenyl group.
[0906] The amide derivative represented by Formula (A1) is
preferably
3-benzamide-N-(2-bromo-6-chloro-4-(heptafluoropropan-2-yl)phenyl)-2-fluor-
obenzamide,
3-benzamide-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenza-
mide,
3-benzamide-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluor-
obenzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenz-
amide)benzamide,
N-(2,6-dichloro-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylben-
zamide)benzamide,
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenza-
mide)benzamide,
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenza-
mide)benzamide,
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenza-
mide)benzamide,
3-(2,6-difluorobenzamide)-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-
-2-fluorobenzamide,
N-(2-bromo-6-iodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylb-
enzamide)benzamide,
[0907]
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluor-
obenzamide)benzamide,
N-(3-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenylcarbamoyl)-2-fluoropheny-
l)-2-fluoro-N-methylbenzamide,
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-me-
thylbenzamide)benzamide,
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluoro-N-me-
thylbenzamide)benzamide,
N-(3-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenylcarbamoyl)-2-fluoropheny-
l)-2,6-difluoro-N-methylbenzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(2-fluorobenz-
amide)benzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluorobenz-
amide)benzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluorobenz-
amide)benzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-3-(2,6-difluorobenzamide-
)-2-fluorobenzamide,
N-(3-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenylcarbamoyl)-2-fluorophen-
yl)-2-fluoro-N-methylbenzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(3-fluoro-N-m-
ethylbenzamide)benzamide,
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(4-fluoro-N-m-
ethylbenzamide)benzamide,
N-(3-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenylcarbamoyl)-2-fluorophen-
yl)-2,6-difluoro-N-methylbenzamide,
[0908]
3-benzamide-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethy-
l)phenyl)-2-fluorobenzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(N-methylbenzamide)benzamide,
3-benzamide-2-fluoro-N-(4-(heptafluoropropan-2-yl)-2,6-bis(trifluoromethy-
l)phenyl)benzamide,
3-benzamide-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromet-
hyl)phenyl)benzamide,
3-benzamide-N-(2-bromo-6-(pentafluoroethyl)-4-(heptafluoropropan-2-yl)phe-
nyl)-2-fluorobenzamide,
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-(N-methylbenzamide)benzamide,
2-fluoro-N-(2-fluoro-3-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromet-
hyl)phenylcarbamoyl)phenyl)-N-methylbenzamide,
2-fluoro-3-(3-fluoro-N-methylbenzamide)-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide,
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide,
2,6-difluoro-N-(2-fluoro-3-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluor-
omethyl)phenylcarbamoyl)phenyl)-N-methylbenzamide,
2-fluoro-3-(2-fluorobenzamide)-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(tr-
ifluoromethyl)phenyl)benzamide,
2-fluoro-3-(3-fluorobenzamide)-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(tr-
ifluoromethyl)phenyl)benzamide,
N-(3-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamo-
yl)-2-fluorophenyl)-2-fluoro-N-methylbenzamide,
N-(3-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenylcarbamo-
yl)-2-fluorophenyl)-2,6-difluoro-N-methylbenzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(3-fluoro-N-methylbenzamide)benzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(4-fluoro-N-methylbenzamide)benzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(2-fluorobenzamide)benzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(3-fluorobenzamide)benzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(4-fluorobenzamide)benzamide,
[0909]
2-fluoro-3-(4-fluorobenzamide)-N-(2-iodo-4-(heptafluoropropan-2-yl)-
-6-(trifluoromethyl)phenyl)benzamide,
3-(2,6-difluorobenzamide)-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-
-(trifluoromethyl)phenyl)benzamide,
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(2,6-d-
ifluorobenzamide)-2-fluorobenzamide,
3-(2,4-dichlorobenzamide)-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-
-(trifluoromethyl)phenyl)benzamide,
3-(2-chloro-4-fluorobenzamide)-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide,
3-(2-chlorobenzamide)-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(tr-
ifluoromethyl)phenyl)benzamide, or
N-(2-chloro-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluor-
o-3-(N-methylbenzamide)benzamide.
[0910] A second aspect of the present invention provides a method
for exterminating animal parasites comprising administering to the
animal the composition for exterminating animal parasites
[0911] Wherein, the animal parasite is preferably an ectoparasite
and the ectoparasite is more preferably Siphonaptera pests or the
ectoparasite is Acarina pests.
[0912] According to the present invention, a composition which has
excellent activity for exterminating animal parasites and a method
for exterminating animal parasites are provided.
[0913] A composition for exterminating animal parasites according
to the present invention includes at least one amide derivative
represented by the following Formula (A1).
[0914] By adopting such a constitution, it becomes possible to show
excellent activity for exterminating animal parasites in the case
of giving the composition to an animal.
##STR00235##
[0915] In Formula (A1), Q.sub.1 represents a phenyl group or a
phenyl group substituted with a halogen atom. X.sub.1 represents a
fluorine atom, and X.sub.2, X.sub.3, and X.sub.4 are each a
hydrogen atom. R.sub.1 represents a hydrogen atom or a C1-C3 alkyl
group, and R.sub.2 is a hydrogen atom. Y.sub.1 and Y.sub.5 each
independently represent a halogen atom or a C1-C3 haloalkyl group,
Y.sub.2 and Y.sub.4 each represent a hydrogen atom, and Y.sub.3
represents a heptafluoroisopropyl group.
[0916] The terms used in the formulae including the Formula (A1)
and the like according to the present invention, have the same
meanings as described below in the definitions.
[0917] The "halogen atom" represents a fluorine atom, a chlorine
atom, a bromine atom, or an iodine atom.
[0918] The expression "Ca-Cb (wherein a and b represent an integer
of 1 or more)", for example, "C1-C3" means the number of carbon
atoms of from 1 to 3, the "C2-C6" means the number of carbon atoms
of from 2 to 6.
[0919] The "C1-C3 alkyl group" in the present invention represents,
for example, a linear or branched alkyl group having from 1 to 3
carbon atoms such as methyl, ethyl, n-propyl, propyl, and the
like.
[0920] The "C1-C3 haloalkyl group" represents, for example, a
linear or branched alkyl group having from 1 to 3 carbon atoms,
that is substituted with one or more halogen atoms which may be the
same as or different from each other, such as trifluoromethyl,
pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl,
2,2-difluoroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl,
2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,
2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2-propyl,
1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl,
1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n-propyl,
1,1,1,3,3,3-hexafluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl,
2,2,3,3,3-pentafluoro-n-propyl, 3-fluoro-n-propyl,
3-chloro-n-propyl, 3-bromo-n-propyl, and the like.
[0921] The "C1-C6 alkyl group" in the present invention represents,
for example, a linear or branched alkyl group having from 1 to 6
carbon atoms such as methyl, ethyl, n-propyl, propyl, n-butyl,
s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2-pentyl,
n-hexyl, 3-methyl-n-pentyl, and the like.
[0922] The "C3-C9 cycloalkyl group" represents, for example, a
cycloalkyl group having from 3 to 9 carbon atoms, that has a cyclic
structure, such as cyclopropyl, cyclobutyl, cyclopentyl,
2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl,
2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, and the
like.
[0923] The "C2-C6 alkenyl group" represents, for example, an
alkenyl group having from 2 to 6 carbon atoms, that has a double
bond in the carbon chain, such as vinyl, allyl, 2-butenyl,
3-butenyl, and the like.
[0924] The "C2-C6 alkynyl group" represents, for example, an
alkynyl group having from 2 to 6 carbon atoms, that has a triple
bond in the carbon chain, such as propargyl, 1-butyn-3-yl,
1-butyn-3-methyl-3-yl, and the like.
[0925] The compounds represented by Formula (A1) according to the
present invention may include one or plural chiral carbon atoms or
chiral centers in their structural Formulae, and thus two or more
optical isomers may exist. However, the present invention includes
each of the optical isomers and a mixture thereof at any
proportions. Further, the compounds represented by Formula (A1)
according to the present invention may include two or more kinds of
geometrical isomers derived from carbon-carbon double bonds in the
structural Formulae. The present invention includes each of the
geometrical isomers and a mixture thereof at any proportions.
[0926] The representative methods for producing the compound
according to the present invention are shown below, and the method
for producing the amide derivative according to the present
invention is not limited to the preparation methods below.
[0927] In Formula shown in the following preparation method,
X.sub.1, X.sub.2, X.sub.3, X.sub.4, R.sub.1, R.sub.2, Q.sub.1,
Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 represent the same
definitions as X.sub.1, X.sub.2, X.sub.3, X.sub.4, R.sub.1,
R.sub.2, Q.sub.1, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5,
respectively, in Formula (A1). LG represents a functional group
having a leaving ability, such as a halogen atom, a hydroxy group,
or the like, Hal represents a chlorine atom or a bromine atom, and
Xa and Xb represent chlorine atoms, bromine atoms, or iodine atoms.
R3 represents a C1-C6 alkyl group, a C3-C9 cycloalkyl group, a
C2-C6 alkenyl group, a C2-C6 alkynyl group.
[0928] <Preparation Method 1>
##STR00236## Formula (A11)+Formula (A12).fwdarw.Formula (A13)
1-(i)
[0929] A nitro aromatic carboxamide derivative represented by
Formula (A13) can be prepared by reacting a nitro aromatic
carboxylic acid derivative having a leaving group represented by
Formula (A11) with an aromatic amine derivative represented by
Formula (A 12) in a suitable solvent or without a solvent. In the
present step, a suitable base can be used.
[0930] The solvent may be any of those which do not inhibit the
present reaction significantly. Examples thereof may include water
and aromatic hydrocarbons such as benzene, toluene, xylene, and the
like, halogenated hydrocarbons such as dichloromethane, chloroform,
carbon tetrachloride, and the like, chained or cyclic ethers such
as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane,
and the like, esters such as ethyl acetate, butyl acetate, and the
like, alcohols such as methanol, ethanol, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, and the
like, amides such as dimethyl formamide, dimethylacetamide, and the
like, nitriles such as acetonitrile and the like, and inert
solvents such as 1,3-dimethyl-2-imidazolidinone and the like. These
solvents may be used alone or as a mixture of two or more kinds
thereof.
[0931] Furthermore, examples of the base may include organic bases
such as triethylamine, tri-n-butyl amine, pyridine, 4-dimethylamino
pyridine, and the like, alkali metal hydroxides such as sodium
hydroxide, potassium hydroxide, and the like, carbonates such as
sodium hydrogen carbonate, potassium carbonate, and the like,
phosphates such as dipotassium monohydrogen phosphate, trisodium
phosphate, and the like, alkali metal hydride salts such as sodium
hydride and the like, alkali metal alkoxides such as sodium
methoxide, sodium ethoxide, and the like, and lithium amides such
as lithium diisopropyl amide, and the like.
[0932] These bases may be appropriately used in an amount in the
range from 0.01-fold molar equivalent to 5-fold molar equivalents
with respect to the compound represented by Formula (A11).
[0933] The reaction temperature may be appropriately selected from
-20.degree. C. to the reflux temperature of the solvent used.
Further, the reaction time may be appropriately selected within the
range from several minutes to 96 hours.
[0934] Among the compounds represented by Formula (A11), the
aromatic carbonyl halide derivative can be prepared easily by a
general method using a halogenating agent from an aromatic
carboxylic acid. Examples of the halogenating agent include thionyl
chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride,
phosphorus trichloride, and the like.
[0935] Meanwhile, it is possible to prepare the compound
represented by Formula (A13) from the nitro aromatic carboxylic
acid derivative and the compound represented by Formula (A12)
without using a halogenating agent. Examples of the method may
include a method described in, for example, Chem. Ber. p. 788
(1970), in which a condensing agent such as
N,N'-dicyclohexylcarbodiimide and the like is appropriately used,
suitably with the use of an additive such as 1-hydroxybenzotriazole
and the like. Other condensing agents that can be used in this case
may include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide,
1,1'-carbonylbis-1H-imidazole, and the like.
[0936] Furthermore, examples of other methods for producing the
compound represented by Formula (A13) may include a mixed acid
anhydride method using chloroformic acid esters, and examples
thereof include a method described in J. Am. Chem. Soc., p. 5012
(1967), whereby the compound represented by Formula (A13) can be
prepared. Examples of the chloroformic acid esters used in this
case may include isobutyl chloroformate, isopropyl chloroformate
and the like. In addition to chloroformic acid esters,
diethylacetyl chloride, trimethylacetyl chloride and the like may
also be included.
[0937] Both the method using a condensing agent and the mixed acid
anhydride method are not limited by the solvent, the reaction
temperature, and the reaction time according to the literature
above. An inert solvent may be used which does not inhibit the
progress of the appropriate reaction significantly, and the
reaction temperature and the reaction time may also be selected
appropriately according to the progress of the reaction.
Formula (A13).fwdarw.Formula (A14) 1-(ii)
[0938] An aromatic carboxamide derivative having an amino group
represented by Formula (A14) can be derived from the aromatic
carboxamide derivative having a nitro group represented by Formula
(A13) by means of a reduction reaction. Examples of such reduction
include a method using a hydrogenation reaction and a method using
a metal compound (for example, stannous chloride (anhydride), iron
powder, zinc powder, and the like).
[0939] The reaction of the former method can be carried out in a
suitable solvent in the presence of a catalyst at normal pressure
or a higher pressure under a hydrogen atmosphere. Examples of the
catalyst may include palladium catalysts such as palladium-carbon
and the like, nickel catalysts such as Raney-nickel and the like,
cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum
catalysts, and the like, and examples of the solvent may include
water; alcohols such as methanol, ethanol, and the like; aromatic
hydrocarbons such as benzene, toluene, and the like; chained or
cyclic ethers such as ether, dioxane, tetrahydrofuran, and the
like; and esters such as ethyl acetate and the like. The pressure
may be appropriately selected within a range of 0.1 MPa to 10 MPa,
the reaction temperature may be appropriately selected within a
range of -20.degree. C. to the reflux temperature of the solvent
used, and the reaction time may be appropriately selected within a
range of several minutes to 96 hours, whereby the compound of
Formula (14) can be efficiently prepared.
[0940] Examples of the latter method include a method using
stannous chloride (anhydride) as a metal compound under the
conditions described in "Organic Syntheses" Coll. Vol. III, P.
453.
Formula (A14).fwdarw.Formula (A15) 1-(iii)
[0941] (Method A)
[0942] A compound represented by Formula (A15) can be prepared by
reacting the compound represented by Formula (A14) with an aldehyde
or a ketone in a solvent, and reacting them under a hydrogen
atmosphere with the addition of a catalyst.
[0943] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, meth yl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as methanol, ethanol, and the
like, inert solvents such as 1,3-dimethyl-2-imidazolidinone,
sulfolane, dimethylsulfoxide, and the like, water, and the like.
These solvents may be used alone or as a mixture of two or more
kinds thereof.
[0944] Examples of the catalyst may include palladium catalysts
such as palladium-carbon, palladium hydroxide-carbon, and the like,
nickel catalysts such as Raney-nickel and the like, cobalt
catalysts, platinum catalysts, ruthenium catalysts, rhodium
catalysts, and the like.
[0945] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, trifluoroacetaldehyde,
difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde,
dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde, and
the like.
[0946] Examples of the ketones may include acetone,
perfluoroacetone, methyl ethyl ketone, and the like.
[0947] The reaction pressure may be appropriately selected within
the range of 1 atm to 100 atm. The reaction temperature may be
appropriately selected within the range from -20.degree. C. to the
reflux temperature of the solvent used. Further, the reaction time
may be appropriately selected within the range from several minutes
to 96 hours.
[0948] (Method B)
[0949] A compound represented by Formula (A15) can be prepared by
reacting the compound represented by Formula (A14) with an aldehyde
or a ketone in a solvent, and treating the product with a reducing
agent.
[0950] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as methanol, ethanol, and the
like, inert solvents such as 1,3-dimethyl-2-imidazolidinone,
sulfolane, dimethylsulfoxide, and the like, water, and the like.
These solvents may be used alone or as a mixture of two or more
kinds thereof.
[0951] Examples of the reducing agent may include, for example,
borohydrides such as sodium borohydride, sodium cyanoborohydride,
sodium triacetate borohydride, and the like.
[0952] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, trifluoroacetaldehyde,
difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde,
dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde, and
the like.
[0953] Examples of the ketones may include acetone,
perfluoroacetone, methyl ethyl ketone, and the like.
[0954] The reaction temperature may be appropriately selected
within the range from -20.degree. C. to the reflux temperature of
the solvent used. Further, the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
[0955] (Method C)
[0956] A compound of Formula (A15) can be prepared by reacting the
compound represented by Formula (A14) with an aldehyde in a solvent
or without a solvent.
[0957] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, xylene, toluene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and the like,
amides such as dimethyl formamide, dimethylacetamide, and the like,
nitriles such as acetonitrile, propionitrile, and the like, ketones
such as acetone, methyl isobutyl ketone, cyclohexanone, methyl
ethyl ketone, and the like, esters such as ethyl acetate, butyl
acetate, and the like, alcohols such as methanol, ethanol, and the
like, inert solvents such as 1,3-dimethyl-2-imidazolidinone,
sulfolane, dimethylsulfoxide, and the like, inorganic acids such as
sulfuric acid, hydrochloric acid, and the like, organic acids such
as formic acid, acetic acid, and the like, water, and the like.
These solvents may be used alone or as a mixture of two or more
kinds thereof.
[0958] Examples of the aldehydes may include formaldehyde,
acetaldehyde, propionaldehyde, and the like.
[0959] The reaction temperature may be appropriately selected
within the range from -20.degree. C. to the reflux temperature of
the solvent used, and the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
Formula (A15)+Formula (A16).fwdarw.Formula (A1) 1-(iv)
[0960] An aromatic carboxamide derivative represented by Formula
(A1) can be prepared by reacting the aromatic amine derivative
represented by Formula (A15) with the carboxylic acid derivative or
the carbonate ester derivative having a leaving group represented
by Formula (A16) in a suitable solvent. In the present step, a
suitable base or solvent can be used, and as the base or solvent,
those exemplified in 1-(i) can be used. Examples of the reaction
temperature, the reaction time, and the like may include those
exemplified in 1-(i).
[0961] In Formula (A16), the carbonyl chloride derivative can be
prepared easily from a carboxylic acid derivative by a general
method using a halogenating agent. The halogenating agent may
include those exemplified in 1-(i).
[0962] There may be exemplified a method for producing a compound
represented by Formula (A1) from the carboxylic acid derivative
(A16) and the compound represented by Formula (A15) without the use
of a halogenating agent, and the preparation can be conducted
according to the method exemplified in 1-(i).
[0963] <Preparation Method 2>
##STR00237## Formula (A17)+Formula (A12).fwdarw.Formula (A18)
2-(i)
[0964] A compound represented by Formula (A18) can be prepared by
reacting the compound represented by Formula (A17) with a compound
represented by Formula (A12) under the condition described in
1-(i).
Formula (A18).fwdarw.Formula (A15) 2-(ii)
[0965] A compound represented by Formula (A15) can be prepared by
carrying out an amination reaction using an amination agent such as
ammonia and the like according to the conditions described, for
example, in J. Org. Chem. p. 280 (1958). However, the conditions
such as a reaction solvent and the like are not restricted to those
described in the literature, and an inert solvent which does not
inhibit the proper progress of the reaction significantly may be
used. The reaction temperature and reaction time may be suitably
selected as the reaction proceeds. Further, examples of the
amination agent include methylamine, ethylamine or the like, in
addition to ammonia.
Formula (A15)+Formula (A16).fwdarw.Formula (A1) 2-(iii)
[0966] The compound represented by Formula (A1) can be prepared by
reacting the compound represented by Formula (A15) with a compound
represented by Formula (A16) according to the conditions described
in 1-(i).
[0967] <Preparation Method 3>
##STR00238## Formula (A19)+Formula (A12).fwdarw.Formula (A20)
3-(i)
[0968] A compound represented by Formula (A20) can be prepared by
reacting the compound represented by Formula (A19) and the compound
represented by Formula (A12) according to the conditions described
in 1-(i).
Formula (A20).fwdarw.Formula (A21) 3-(ii)
[0969] A compound represented by Formula (A21) can be prepared by
reacting the nitro aromatic carboxamide derivative represented by
Formula (A20) with a suitable fluorinating agent in a suitable
solvent or without a solvent.
[0970] The solvent may be any of those which do not inhibit the
progress of the reaction significantly, and examples thereof may
include aliphatic hydrocarbons such as hexane, cyclohexane,
methylcyclohexane, and the like, aromatic hydrocarbons such as
benzene, toluene, xylene, and the like, halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and the like, chained or cyclic ethers such as
diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, and
the like, esters such as ethyl acetate, butyl acetate, and the
like, ketones such as acetone, methyl isobutyl ketone,
cyclohexanone, methyl ethyl ketone, and the like, nitriles such as
acetonitrile, propionitrile, and the like, and aprotic polar
solvents such as 1,3-dimethyl-2-imidazolidinone, sulfolane,
dimethylsulfoxide, N,N-dimethyl formamide, N-methylpyrrolidone,
N,N-dimethylacetamide, and the like. These solvents may be used
alone or as a mixture of two or more kinds thereof.
[0971] Examples of the fluorinating agent may include
1,1,2,2-tetrafluoroethyl diethylamine,
2-chloro-1,1,2-trifluoroethyl diethylamine,
trifluorodiphenylphospholane, difluorotriphenylphospholane,
fluoroformic acid esters, sulfur tetrafluoride, potassium fluoride,
potassium hydrogen fluoride, cesium fluoride, rubidium fluoride,
sodium fluoride, lithium fluoride, antimony (III) fluoride,
antimony (V) fluoride, zinc fluoride, cobalt fluoride, lead
fluoride, copper fluoride, mercury (II) fluoride, silver fluoride,
silver fluoroborate, thallium (I) fluoride, molybdenum (VI)
fluoride, arsenic (III) fluoride, bromine fluoride, selenium
tetrafluoride, tris(dimethylamino)sulfonium
difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary
ammonium fluorides, (2-chloroethyl) diethylamine,
diethylaminosulfur trifluoride, morpholinosulfur trifluoride,
silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid,
hydrogen fluoride-pyridine complex, hydrogen fluoride-triethylamine
complex, hydrogen fluoride salts, bis(2-methoxyethyl)amino
sulfurtrifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone,
iodine pentafluoride, tris(diethylamino)phosphonium
2,2,3,3,4,4-hexafluorocyclobutanilide, triethylammonium
hexafluorocylcobutanilide, hexafluoropropene, and the like. These
fluorinating agents may be used alone or as a mixture of two or
more kinds thereof.
[0972] The fluorinating agent may be appropriately selected and
used as a solvent, in the range of 1-fold molar equivalent to
10-fold molar equivalents with respect to the nitro aromatic
carboxamide derivative represented by Formula (A20).
[0973] Additives may be used, and examples thereof may include
crown ethers such as 18-crown-6 and the like, phase transfer
catalysts such as a tetraphenylphosphonium salt and the like,
inorganic salts such as calcium fluoride, calcium chloride, and the
like, metal oxides such as mercury oxide and the like, ion exchange
resins, and the like. These additives may not only be added to the
reaction system but also used as a pretreating agent for the
fluorinating agent.
[0974] The reaction temperature may be appropriately selected
within the range from -80.degree. C. to the reflux temperature of
the solvent used, and the reaction time may be appropriately
selected within the range from several minutes to 96 hours.
[0975] <Preparation Method 4>
##STR00239## Formula (A22)+Formula (A16).fwdarw.Formula (A23)
4-(i)
[0976] A carboxylic acid having an acylamino group represented by
Formula (A23) can be prepared by reacting a compound represented by
Formula (A22) as a starting material with a compound represented by
Formula (A16) according to the conditions described in 1-(i).
Formula (A23)+Formula (A24).fwdarw.Formula (A25) 4-(ii)
[0977] The compound represented by Formula (A25) can be prepared by
reacting the amide compound represented by Formula (A23) with the
compound having a leaving group such as a halogen and the like,
represented by Formula (A24) in a solvent or without a solvent. In
the present step, a suitable base or solvent can be used, and as
the base or solvent, those exemplified in 1-(i) can be used.
Examples of the reaction temperature, the reaction time, and the
like may include those exemplified in 1-(i).
Formula (A25).fwdarw.Formula (A26) 4-(iii)
[0978] The compound represented by Formula (A26) can be prepared
from the compound represented by Formula (A25) through hydrolysis
conducted by a general technique or a method using a Pd catalyst.
In the hydrolysis, the compound can be obtained by base hydrolysis
using one equivalent to 5-fold molar amount of aqueous or alcoholic
lithium hydroxide, sodium hydroxide, or potassium hydroxide in a
single solvent of methanol, ethanol, tetrahydrofuran, or dioxane,
or a combination thereof. Also in a non-aqueous solvent such as
toluene and xylene, hydrolysis can be conducted with the
combination of a base such as aqueous sodium hydroxide, potassium
hydroxide, or lithium hydroxide and a phase-transfer catalyst such
as tetrabutylammonium bromide, benzyltriethylammonium chloride, or
crown ether. Alternatively, acid hydrolysis can be conducted with
inorganic acid such as hydrochloric acid and sulfuric acid, organic
acid such as acetic acid and trifluoroacetic acid, or strongly
acidic resin.
[0979] The reaction temperature may be appropriately selected in
the range from -20.degree. C. to the reflux temperature of the
solvent to be used. And the reaction time may be appropriately
selected in the range from a few minutes to 96 hours.
[0980] The method using Pd can include, for example, the method
described in Tetrahedron Letters p. 4371 (1987). The conditions
such as the solvent and the reaction temperature are not limited to
those described in the reference.
Formula (A26).fwdarw.Formula (A27) 4-(iv)
[0981] The compound represented by Formula (A27) can be prepared
according to the known routine procedure in which the compound
represented by Formula (A26) is reacted with thionyl chloride,
oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus
pentachloride, phosphorous trichloride, thionyl bromide, phosphorus
tribromide, diethylaminosulfur trifluoride, or the like.
Formula (A27)+Formula (A12).fwdarw.Formula (A1) 4-(v)
[0982] The compound represented by Formula (A1) can be produced by
reacting the compound represented by Formula (A27) with the
compound represented by Formula (A12) according to the conditions
described in 1-(i).
Formula (A26)+Formula (A12).fwdarw.Formula (A1) 4-(vi)
[0983] The amide derivative represented by Formula (A1) can be
produced by reacting the compound represented by Formula (A26) with
the compound represented by Formula (A12) according to the
conditions of the method in which a condensing agent is used or the
mixed anhydride method both described in 1-(i).
[0984] <Production Method 5>
##STR00240## Formula (A28).fwdarw.Formula (A29) 5-(i)
[0985] The compound represented by Formula (A29) can be produced by
fluorinating the compound represented by Formula (A28) according to
the conditions described in 3-(ii).
Formula (A29).fwdarw.Formula (A30) 5-(ii)
[0986] The compound represented by Formula (A30) can be produced by
reducing the compound represented by Formula (A29) according to the
conditions described in 1-(ii).
[0987] In all of the preparation methods as described above, a
desired product may be isolated from the reaction system after the
reaction is completed according to a general method, but if
required, purification can be carried out by operations such as
recrystallization, column chromatography, distillation, and the
like. In addition, the desired product can be also provided to the
subsequent reaction process without being separated from the
reaction system.
[0988] Hereinbelow, examples of the representative compounds of the
amide derivative represented by Formula (A1) as an active
ingredient for the composition for exterminating animal parasites
according to the present invention will be given in Table A1 and
Table A2 below, but the present invention is not limited
thereto.
[0989] In addition, in the tables, "Me" represents a methyl group,
"n-Pr" represents a normal propyl group, "CF3" represents a
trifluoromethyl group, "C2F5" represents a pentafluoroethyl group,
"n-C3F7" represents a heptafluoronormalpropyl group, "H" represents
a hydrogen atom, "F" represents a fluorine atom, "Cl" represents a
chlorine atom, "Br" represents a bromine atom, and "I" represents
an iodine atom, respectively.
TABLE-US-00053 TABLE A1 ##STR00241## compound number Q.sub.1
R.sub.1 R.sub.2 X.sub.1 X.sub.2 X.sub.3 X.sub.4 Y.sub.1 Y.sub.2
Y.sub.3 Y.sub.4 Y.sub.5 6-940 phenyl H H F H H H F H
heptafluoroisopropyl H F 6-948 phenyl H H F H H H Cl H
heptafluoroisopropyl H Cl 6-952 2-chlorophenyl H H F H H H F H
heptafluoroisopropyl H Cl 6-956 3-bromophenyl H H F H H H F H
heptafluoroisopropyl H Br 6-970 2,6-difluorophenyl H H F H H H Cl H
heptafluoroisopropyl H I 6-1104 phenyl H H F H H H Br H
heptafluoroisopropyl H Br 6-1105 2-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H Br 6-1106 3-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H Br 6-1107 4-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H Br 6-1126 2,6-difluorophenyl H H F H H H Br
H heptafluoroisopropyl H Br 6-1260 phenyl H H F H H H I H
heptafluoroisopropyl H I 6-1261 2-fluorophenyl H H F H H H I H
heptafluoroisopropyl H I 6-1262 3-fluorophenyl H H F H H H I H
heptafluoroisopropyl H I 6-1263 4-fluorophenyl H H F H H H I H
heptafluoroisopropyl H I 6-1282 2,6-difluorophenyl H H F H H H I H
heptafluoroisopropyl H I 6-1416 phenyl H H F H H H F H
heptafluoroisopropyl H CF3 6-1417 phenyl H H F H H H Cl H
heptafluoroisopropyl H CF3 6-1418 2-fluorophenyl H H F H H H Cl H
heptafluoroisopropyl H CF3 6-1422 3-chlorophenyl H H F H H H Cl H
heptafluoroisopropyl H CF3 6-1426 4-bromophenyl H H F H H H Cl H
heptafluoroisopropyl H CF3 6-1439 2,6-difluorophenyl H H F H H H Cl
H heptafluoroisopropyl H CF3 6-1440 3,4-dichlorophenyl H H F H H H
Cl H heptafluoroisopropyl H CF3 6-1441 2,4-dichlorophenyl H H F H H
H Cl H heptafluoroisopropyl H C2F5 6-1442 2-chloro-4-fluorophenyl H
H F H H H Cl H heptafluoroisopropyl H CF3 6-1445
2-bromo-4-chlorophenyl H H F H H H Cl H heptafluoroisopropyl H
n-C3F7 6-1446 2-bromo-4-fluorophenyl H H F H H H Cl H
heptafluoroisopropyl H CF3 6-1574 phenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1575 2-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1576 3-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1577 4-fluorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1578 2-chlorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1579 3-chlorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1580 4-chlorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1581 2-bromophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1582 3-bromophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1583 4-bromophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1584 2-iodophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1585 3-iodophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1586 4-iodophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1596 2,6-difluorophenyl H H F H H H Br
H heptafluoroisopropyl H CF3 6-1597 3,4-dichlorophenyl H H F H H H
Br H heptafluoroisopropyl H CF3 6-1598 2,4-dichlorophenyl H H F H H
H Br H heptafluoroisopropyl H CF3 6-1599 2-chloro-4-fluorophenyl H
H F H H H Br H heptafluoroisopropyl H CF3 6-1600
2-chloro-4,5-difluorophenyl H H F H H H Br H heptafluoroisopropyl H
CF3 6-1601 4-bromo-2-chlorophenyl H H F H H H Br H
heptafluoroisopropyl H CF3 6-1602 2-bromo-4-chlorophenyl H H F H H
H Br H heptafluoroisopropyl H CF3 6-1603 2-bromo-4-fluorophenyl H H
F H H H Br H heptafluoroisopropyl H CF3 6-1730 phenyl H H F H H H I
H heptafluoroisopropyl H CF3 6-1731 2-fluorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1732 3-fluorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1733 4-fluorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1734 2-chlorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1735 3-chlorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1736 4-chlorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1737 2-bromophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1738 3-bromophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1739 4-bromophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1740 2-iodophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1741 3-iodophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1742 4-iodophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1752 2,6-difluorophenyl H H F H H H I
H heptafluoroisopropyl H CF3 6-1753 3,4-dichlorophenyl H H F H H H
I H heptafluoroisopropyl H CF3 6-1754 2,4-dichlorophenyl H H F H H
H I H heptafluoroisopropyl H CF3 6-1755 2-chloro-4-fluorophenyl H H
F H H H I H heptafluoroisopropyl H CF3 6-1756
2-chloro-4,5-difluorophenyl H H F H H H I H heptafluoroisopropyl H
CF3 6-1757 4-bromo-2-chlorophenyl H H F H H H I H
heptafluoroisopropyl H CF3 6-1758 2-bromo-4-chlorophenyl H H F H H
H I H heptafluoroisopropyl H CF3 6-1759 2-bromo-4-fluorophenyl H H
F H H H I H heptafluoroisopropyl H CF3 6-2110 phenyl H H F H H H
CF3 H heptafluoroisopropyl H CF3 6-5902 phenyl H H F H H H Br H
heptafluoroisopropyl H Cl 6-5910 phenyl H H F H H H Br H
heptafluoroisopropyl H C2F5
TABLE-US-00054 TABLE A2 ##STR00242## compound number Q.sub.1
R.sub.1 R.sub.2 X.sub.1 X.sub.2 X.sub.3 X.sub.4 Y.sub.1 Y.sub.2
Y.sub.3 Y.sub.4 Y.sub.5 7-940 phenyl Me H F H H H F H
heptafluoroisopropyl H F 7-948 phenyl Me H F H H H Cl H
heptafluoroisopropyl H Cl 7-1104 phenyl Me H F H H H Br H
heptafluoroisopropyl H Br 7-1105 2-fluorophenyl Me H F H H H Br H
heptafluoroisopropyl H Br 7-1106 3-fluorophenyl Me H F H H H Br H
heptafluoroisopropyl H Br 7-1107 4-fluorophenyl Me H F H H H Br H
heptafluoroisopropyl H Br 7-1126 2,6-difluorophenyl Me H F H H H Br
H heptafluoroisopropyl H Br 7-1260 phenyl Me H F H H H I H
heptafluoroisopropyl H I 7-1261 2-fluorophenyl Me H F H H H I H
heptafluoroisopropyl H I 7-1262 3-fluorophenyl Me H F H H H I H
heptafluoroisopropyl H I 7-1263 4-fluorophenyl Me H F H H H I H
heptafluoroisopropyl H I 7-1282 2,6-difluorophenyl Me H F H H H I H
heptafluoroisopropyl H I 7-1416 phenyl Me H F H H H F H
heptafluoroisopropyl H CF3 7-1417 phenyl Me H F H H H Cl H
heptafluoroisopropyl H CF3 7-1441 2,4-dichlorophenyl Me H F H H H
Cl H heptafluoroisopropyl H C2F5 7-1442 2-chloro-4-fluorophenyl
n-Pr H F H H H Cl H heptafluoroisopropyl H CF3 7-1445
2-bromo-4-chlorophenyl Me H F H H H Cl H heptafluoroisopropyl H
n-C3F7 7-1574 phenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1575 2-fluorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1576 3-fluorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1577 4-fluorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1578 2-chlorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1579 3-chlorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1580 4-chlorophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1581 2-bromophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1582 3-bromophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1583 4-bromophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1584 2-iodophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1585 3-iodophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1586 4-iodophenyl Me H F H H H Br H heptafluoroisopropyl H CF3
7-1596 2,6-difluorophenyl Me H F H H H Br H heptafluoroisopropyl H
CF3 7-1597 3,4-dichlorophenyl Me H F H H H Br H
heptafluoroisopropyl H CF3 7-1598 2,4-dichlorophenyl Me H F H H H
Br H heptafluoroisopropyl H CF3 7-1599 2-chloro-4-fluorophenyl Me H
F H H H Br H heptafluoroisopropyl H CF3 7-1600
2-chloro-4,5-difluorophenyl Me H F H H H Br H heptafluoroisopropyl
H CF3 7-1601 4-bromo-2-chlorophenyl Me H F H H H Br H
heptafluoroisopropyl H CF3 7-1602 2-bromo-4-chlorophenyl Me H F H H
H Br H heptafluoroisopropyl H CF3 7-1603 2-bromo-4-fluorophenyl Me
H F H H H Br H heptafluoroisopropyl H CF3 7-1730 phenyl Me H F H H
H I H heptafluoroisopropyl H CF3 7-1731 2-fluorophenyl Me H F H H H
I H heptafluoroisopropyl H CF3 7-1732 3-fluorophenyl Me H F H H H I
H heptafluoroisopropyl H CF3 7-1733 4-fluorophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1734 2-chlorophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1735 3-chlorophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1736 4-chlorophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1737 2-bromophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1738 3-bromophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1739 4-bromophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1740 2-iodophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1741 3-iodophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1742 4-iodophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1752 2,6-difluorophenyl Me H F H H H I
H heptafluoroisopropyl H CF3 7-1753 3,4-dichlorophenyl Me H F H H H
I H heptafluoroisopropyl H CF3 7-1754 2,4-dichlorophenyl Me H F H H
H I H heptafluoroisopropyl H CF3 7-1755 2-chloro-4-fluorophenyl Me
H F H H H I H heptafluoroisopropyl H CF3 7-1756
2-chloro-4,5-difluorophenyl Me H F H H H I H heptafluoroisopropyl H
CF3 7-1757 4-bromo-2-chlorophenyl Me H F H H H I H
heptafluoroisopropyl H CF3 7-1758 2-bromo-4-chlorophenyl Me H F H H
H I H heptafluoroisopropyl H CF3 7-1759 2-bromo-4-fluorophenyl Me H
F H H H I H heptafluoroisopropyl H CF3 7-2110 phenyl Me H F H H H
CF3 H heptafluoroisopropyl H CF3 7-5902 phenyl Me H F H H H I H
heptafluoroisopropyl H Br
[0990] Hereinbelow, Table A3 shows the physical properties of the
representative compounds of the amide derivative according to the
present invention. The .sup.1H-NMR chemical shift values shown
therein are based on tetramethylsilane as an internal standard
substance unless specified otherwise.
TABLE-US-00055 TABLE A3 compound number .sup.1H-NMR (CDCl.sub.3,
ppm) 6-1104 .delta. 7.40 (1H, t, J = 7.8 Hz), 7.53-7.64 (3H, m),
7.89 (2H, s), 7.90-7.95 (3H, m), 8.11-8.14 (2H, m), 8.69-8.70 (1H,
m). 6-1105 .delta. 7.22-7.26 (1H, m), 7.35-7.41 (2H, m), 7.58 (1H,
d, J = 8.0 Hz), 7.88-7.92 (3H, m), 8.15-8.25 (2H, m), 8.74-8.75
(2H, m). 6-1106 .delta. 7.35-7.34 (1H, m), 7.417.42 (1H, m),
7.53-7.54 (1H, m), 7.67-7.68 (2H, m), 7.89-7.90 (3H, m), 8.09-8.10
(2H, m), 8.66-8.68 (1H, m). 6-1107 .delta. 7.21-7.26 (2H, m),
7.39-7.41 (1H, m), 7.89-7.96 (4H, m), 8.05-8.13 (3H, m), 8.70-8.72
(1H, m). 6-1126 .delta. 7.05-7.09 (2H, m), 7.38-7.42 (1H, m),
7.49-7.50 (1H, m), 7.88-7.99 (4H, m), 8.09-8.12 (1H, m), 8.71-8.72
(1H, m). 6-1260 .delta. 7.39 (1H, t, J = 7.8 Hz), 7.52-7.57 (4H,
m), 7.60-7.63 (2H, m), 7.93-7.94 (4H, m), 8.70 (1H, t, J = 6.3 Hz).
6-1261 .delta. 7.22-7.28 (1H, m), 7.35-7.42 (2H, m), 7.59-7.61 (1H,
m), 7.94-7.95 (1H, m), 8.12 (2H, s), 8.15-8.25 (2H, m), 8.78 (1H,
t, J = 1.5 Hz), 9.00 (1H, d, J = 7.8 Hz). 6-1262 .delta. 7.30-7.33
(1H, m), 7.40-7.44 (1H, m), 7.52-7.55 (2H, m), 7.64-7.70 (3H, m),
7.95-7.96 (1H, m), 8.09-8.13 (2H, m), 8.67-8.68 (1H, m). 6-1263
.delta. 7.20-7.26 (3H, m), 7.38-7.42 (1H, m), 7.91-7.98 (3H, m),
8.07-8.12 (3H, m), 8.63-8.67 (1H, m). 6-1282 .delta. 7.06 (2H, t, J
= 8.3 Hz), 7.38-7.42 (1H, m), 7.47-7.52 (1H, m), 7.93-7.97 (1H, m),
8.01 (1H, s), 8.11-8.13 (3H, m), 8.68-8.72 (1H, m). 6-1574 .delta.
7.37-7.41 (1H, m), 7.53-7.64 (3H, m), 7.86-7.94 (4H, m), 8.13-8.22
(3H, m), 8.67-8.72 (1H, m). 6-1575 .delta. 7.22-7.27 (1H, m),
7.35-7.41 (2H, m), 7.57-7.60 (1H, m), 7.88-7.93 (2H, m), 8.16 (1H,
s), 8.20-8.25 (2H, m), 8.74-8.75 (1H, m), 8.77-9.00 (1H, m). 6-1576
.delta. 7.27-7.37 (2H, m), 7.48-7.53 (1H, m), 7.72-7.80 (3H, m),
7.92 (1H, s), 8.15 (1H, s), 8.27-8.31 (1H, m), 9.16 (1H, s), 9.35
(1H, d, J = 7.3 Hz). 6-1577 .delta. 7.20-7.23 (3H, m), 7.24-7.26
(1H, m), 7.39-7.40 (3H, m), 7.86-7.97 (1H, m), 8.06 (1H, d, J = 2.4
Hz), 8.16-8.20 (1H, m), 8.62-8.67 (1H, m). 6-1596 .delta. 7.00-7.09
(2H, m), 7.40-7.41 (1H, m), 7.46-7.53 (1H, m), 7.89-7.92 (2H, m),
8.00 (1H, s), 8.16-8.19 (2H, m), 8.71-8.72 (1H, m). 6-1730 .delta.
7.40 (1H, t, J = 7.8 Hz), 7.53-7.64 (3H, m), 7.87-7.95 (4H, m),
8.14 (1H, s), 8.22 (1H, d, J = 12.7 Hz), 8.37 (1H, s), 8.71-8.72
(1H, m). 6-1731 .delta. 7.22-7.25 (1H, m), 7.35-7.37 (2H, m),
7.58-7.60 (1H, m), 7.90 (1H, t, J = 8.6 Hz), 7.96 (1H, s), 8.22
(1H, t, J = 8.8 Hz), 8.29-8.32 (1H, d, J = 12.4 Hz), 8.37 (1H, s),
8.73 (1H, m), 8.94 (1H, s). 6-1732 .delta. 7.32-7.33 (1H, m), 7.37
(1H, t, J = 8.0 Hz), 7.52-7.54 (1H, m), 7.64-7.70 (2H, m), 7.90
(1H, t, J = 6.4 Hz), 7.96 (1H, s), 8.10 (1H, s), 8.23 (1H, d, J =
12.0 Hz), 8.37 (1H, s), 8.65 (1H, t, J = 8.0 Hz). 6-1733 .delta.
7.19-7.25 (2H, m), 7.35 (1H, t, J = 7.8 Hz), 7.87-7.97 (4H, m),
8.08 (1H, s), 8.25 (1H, d, J = 12.0 Hz), 8.37 (1H, s), 8.65 (1H, t,
J = 8.0 Hz). 6-1734 .delta. 7.43-7.52 (5H, m), 7.87-7.95 (3H, m),
8.22 (1H, d, J = 10.0 Hz), 8.35 (1H, d, J = 8.2 Hz), 8.74 (1H, t, J
= 8.4 Hz). 6-2110 .delta. 7.36-7.40 (1H, m), 7.53-7.64 (3H, m),
7.84-7.97 (1H, m), 7.92-7.94 (2H, m), 8.04-8.07 (1H, m), 8.08-8.13
(1H, m), 8.20 (2H, s), 8.68-8.72 (1H, m). 6-5902 (DMSO-d.sub.6)
.delta. 7.39 (1H, t, J = 7.8 Hz), 7.52-7.64 (4H, m), 7.81 (1H, t, J
= 6.8 Hz), 7.95 (1H, s), 7.98-8.01 (3H, m), 10.29 (1H, s), 10.68
(1H, s). 6-5910 .delta. 7.39 (1H, t, J = 8.3 Hz), 7.53-7.64 (3H,
m), 7.88-7.94 (4H, m), 8.13 (1H, broad-s), 8.19 (1H, broad-s), 8.24
(1H, d, J = 13.2 Hz), 8.70-8.72 (1H, m). 7-948 .delta. 3.49 (3H,
s), 7.23-7.52 (8H, m), 7.66 (2H, s), 8.00 (1H, t, J = 6.8 Hz).
7-1104 .delta. 3.51 (3H, s), 7.22-7.44 (7H, m), 7.86 (2H, s),
8.00-8.03 (2H, m). 7-1105 .delta. 3.52 (3H, s), 6.82 (1H, t, J =
8.8 Hz), 7.06-7.08 (1H, m), 7.18-7.24 (2H, m), 7.40-7.44 (2H, m),
7.87 (3H, s), 8.01-8.05 (1H, m). 7-1106 .delta. 3.50 (3H, s),
7.00-7.23 (4H, m), 7.29-7.31 (1H, m), 7.45 (1H, s), 7.87 (3H, s),
8.03-8.07 (1H, m). 7-1107 .delta. 3.49 (3H, s), 6.91-6.93 (2H, m),
7.28-7.44 (4H, m), 7.86 (2H, s), 8.00-8.10 (2H, m). 7-1126 .delta.
3.49 (3H, s), 6.72-6.76 (2H, m), 7.16-7.23 (2H, m), 7.43-7.50 (1H,
m), 7.88 (2H, s), 8.02-8.06 (1H, m), 8.13-8.17 (1H, m). 7-1260
.delta. 4.09 (3H, s), 7.21-7.49 (7H, m), 7.99-8.08 (4H, m). 7-1261
.delta. 3.53 (3H, s), 6.79-6.83 (1H, m), 7.03-7.07 (1H, m),
7.19-7.23 (2H, m), 7.42-7.43 (2H, m), 8.01-8.10 (4H, m). 7-1417
.delta. 3.49 (3H, s), 7.23-7.26 (3H, m), 7.27-7.33 (3H, m),
7.52-7.53 (1H, m), 7.85 (1H, s), 7.96-8.06 (3H, m). 7-1574 .delta.
3.50 (3H, s), 6.99-7.33 (6H, m), 7.43-7.45 (1H, m), 7.90 (1H, s),
7.97-8.06 (2H, m), 8.13 (1H, s). 7-1575 .delta. 3.52 (3H, s),
6.82-6.83 (1H, m), 7.06-7.07 (1H, m), 7.19-7.26 (2H, m), 7.39-7.46
(2H, m), 7.91 (1H, s), 7.99-8.01 (1H, m), 8.07-8.14 (2H, m). 7-1576
.delta. 3.50 (3H, s), 7.01-7.17 (4H, m), 7.27-7.31 (1H, m),
7.46-7.52 (1H, m), 7.91 (1H, s), 8.01-8.05 (2H, m), 8.13 (1H, s).
7-1577 .delta. 3.50 (3H, s), 6.90-6.94 (2H, m), 7.26-7.35 (3H, m),
7.45-7.46 (1H, m), 7.90 (1H, s), 8.00-8.07 (2H, m), 8.13 (1H, s).
7-1596 .delta. 3.54 (3H, s), 6.75 (2H, broad-s), 7.17-7.26 (2H, m),
7.50-7.51 (1H, m), 7.92 (1H, s), 8.01-8.05 (1H, m), 8.14-8.20 (2H,
m). 7-1730 .delta. 3.51 (3H, s), 7.21-7.23 (2H, m), 7.27-7.33 (4H,
m), 7.44-7.46 (1H, m), 7.92 (1H, s), 8.00 (1H, t, J = 6.3 Hz),
8.08-8.09 (1H, m), 8.33 (1H, s). 7-1731 .delta. 3.51 (3H, s),
6.79-6.83 (1H, m), 7.05 (1H, t, J = 7.6 Hz), 7.18-7.46 (4H, m),
7.94-8.00 (2H, m), 8.20 (1H, d, J = 12.4 Hz), 8.34 (1H, s). 7-1732
.delta. 3.50 (3H, s), 7.00-7.18 (4H, m), 7.27-7.31 (1H, m),
7.45-7.48 (1H, m), 7.93 (1H, s), 8.01-8.03 (1H, m), 8.12 (1H,
broad-s), 8.34 (1H, s). 7-1733 .delta. 3.50 (3H, s), 6.91 (2H, s),
6.93-7.35 (3H, m), 7.47 (1H, t, J = 7.0 Hz), 7.93 (1H, s),
8.01-8.10 (1H, m), 8.13 (1H, broad-s), 8.34 (1H, s). 7-1752 .delta.
3.54 (3H, s), 6.74 (2H, s), 7.16-7.24 (2H, m), 7.50 (1H, t, J = 7.4
Hz), 7.94 (1H, s), 8.01-8.05 (1H, m), 8.25 (1H, broad-s), 8.35 (1H,
s). 7-5902 .delta. 3.51 (3H, s), 7.00-7.52 (7H, m), 7.88 (1H, d, J
= 1.5 Hz), 8.01-8.06 (3H, m).
[0991] In particular, for example, animal parasites that can be
exterminated by the composition for exterminating animal parasites
according to the invention include the followings, although the
invention is not limited thereto.
[0992] The ectoparasites include Siphonaptera pests such as
Ctenocephalides fells, Ctenocephalides canis, Xenopsylla cheopis,
Echidnophaga gallinacea), and Pulex irritans;
[0993] acarine pests such as Haemaphyxalis longicornis,
Haemaphysalis japonica, Rhipicephalus sanguineus, Boophilus
microplus, Dermacentor recticulatus, Dermacentor taiwanensis,
Haemaphysalis flava, Ixodes ovatus, Ixodes persulcatus, Amblyomma
americanum, Amblyomma maculatum, Dermacentor andersoni, Dermacentor
occidentalis, Dermacentor variabilis, Haemaphysalis campanulata,
Haemaphysalis megaspinosa, Ixodes nipponensis, Ixodes pacifcus,
Ixodes ricinus, and Ixodes scapularisand;
[0994] dipterous pests such as Musca hervei, Musca bezzii,
Haematobia irritans, Simulium iwatens, Culicoides oxystoma, Tabanus
chrysurus, Culex pipiens, and Aedes albopictus;
[0995] Phthiraptera pests such as Haematopinus eurysternus and
Damalinia ovis; and the like.
[0996] The endoparasites include:
[0997] Protozoa such as Rhizopoda including Endamoeba histolytica,
Mastigophora including Leishmania and Trichomonas, Sporozoea
including Plasmodium and Toxoplasma, and Ciliophora including
Balantidium coli;
[0998] helminths such as Nematoda including Ascaris lumbricoides
and Ancylostoma, Acannthocephala including Macracanthorhynchus
hirudinaceus, Nematomorpha including Paragordius tricuspidatus,
Trematoda including Clonorchis sinensis, and Cestoda including
Taenia saginata;
[0999] nematodes such as Ascaris, Toxocara, Toxascaris, Parascaris,
Ascaridia, Heterakis, Oxyuris, Capillaria, Trichinella, Strongylus,
Triodontophorus, Trichonema, Stephanurus, Desophagostomum,
Chabertia, Syngamus, Ancylostoma, Uncinaria, Necator, Bunostomum,
Trichostrongylus, Cooperia, Nematodirus, Haemonchus, Ostertagia,
Dictyocaulus, Metastrongylus, Dirofilaria, Parafilaria, Setaria,
Onchocerca, Habronema, Arduenna, and Acuaria;
[1000] cestodes such as Diphyllobothrium, Anoplocephara, Moniezia,
Dipylidium, Taenia, Dithyridium, Raillietina, and Echinococcus;
[1001] flukes such as Schistosoma, Paramphistomum, and Fasciola;
and the like.
[1002] In the invention, said animal parasites are preferably
ectoparasites from the viewpoint of parasiticidal activity, and
they are preferably at least one of Siphonaptera pests (especially
preferably Ctenocephalides felis) and Acarina pests (especially
preferably Haemaphyxalis longicornis, Rhipicephalus sanguineus, and
Boophilus microplus).
[1003] The animals to which the composition for exterminating
animal parasites according to the invention can be applied include
domestic animals such as human, horses, cows, pigs, sheep, goats,
rabbits, camels, buffalos, deer, minks, and chinchillas; fowls such
as chickens, ducks, geese, and turkeys; pets such as dogs, cats,
small birds, and monkeys; laboratory animals such as rats, mice,
golden hamsters, and guinea pigs; and the like, although the
invention is not limited thereto.
[1004] The composition for exterminating animal parasites according
to the invention can be used as a parasiticide by any of the
methods normally used, with no particular restriction.
[1005] In particular, for example, the composition may be
dissolved, suspended, mixed, impregnated, adsorbed, or adhered on
suitable solid and/or liquid carriers according to a formulation
generally used, and, if required, together with adjuvant in a
suitable proportion. And the composition may be prepared into an
appropriate form in accordance with the intended use.
[1006] The solid or liquid carrier for use in the invention may be
those normally used in agents for animals. From the viewpoint of
easiness of treatment on the target animals, it is preferable to
use a liquid carrier. The liquid carrier includes, for example,
alcohol such as methyl alcohol, ethyl alcohol, isopropyl alcohol,
tertiary butyl alcohol, and benzyl alcohol; propylene carbonate;
N-methyl-2-pyrrolidone; water; and the like. As the adjuvant,
surfactant, antioxidant, emulsifier, and the like can be used. The
adjuvant can include, for example, surfactant such as
polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan
monolaurate, alkyl allyl sorbitan monolaurate,
alkylbenzenesulfonate, alkylnaphthalene sulfonic acid,
ligninsulfonic acid salts, higher alcohol sulfate salts, glycol
monoalkyl ethers, and glycols; emulsifier such as sorbitan
monooleate, sorbitan monolaurate, caprylic acid monoglyceride,
capric acid monoglyceride, isostearic acid monoglyceride, and
propylene glycol monocaprylate; and antioxidant such as BHA and
BHT.
[1007] The composition for exterminating animal parasites according
to the invention may be administered orally or parenterally to an
animal.
[1008] If the composition for exterminating animal parasites
according to the invention is administered orally, the composition
may be in the form of capsules, tablets, pills, powders, granules,
fine granules, syrups, enteric agents, suspensions, paste, or
beverage or feeds mixed with the drug.
[1009] If the composition for exterminating animal parasites
according to the invention is administered parenterally, the
composition may be in the form of injectables, drips,
suppositories, emulsions, suspensions, drops, ointments, creams,
solutions, lotions, sprays, aerosols, cataplasms, and tapes.
[1010] The method for administration includes the spot-on method in
which drops are dropped on the skin of the back shoulder region and
the like of the target animal to exterminate ectoparasites; local
methods such as the pour-on method in which a liquid agent is
applied along the back center line of the target animal to allow
the applied agent to diffuse on the body surface, resulting in
control of ectoparasites; the methods in which the agent is
released from a collar containing the agent; the methods in which a
liquid agent, ointment, or the like is directly applied to the body
surface; the methods in which an aerosol or the like is applied
with a spray or the like; the methods in which an injectable is
injected intramuscularly, subcutaneously, or the like; and rectal
administration with a suppository.
[1011] In addition to extermination of endoparasites and
exoparasites, the composition for exterminating animal parasites
according to the invention also can prophylactically prevent
parasitic infections by applying it to the environments which are
to be the infection routes. For example, the composition can
prevent soil infections from soils of upland fields and parks;
percutaneous infections from aqueous systems such as river, lake,
wetland, and paddy field; oral infections from excrements of
animals such as dogs and cats; and oral infections from raw meats
of sea water fish, fresh water fish, Crustaceae, shellfish,
domestic animals, and the like; and infections from mosquitoes,
horseflies, flies, cockroaches, ticks, fleas, lice, assassin bugs,
chiggers, etc.; and the like.
[1012] If the composition for exterminating animal parasites
according to the invention is used to exterminate parasites in the
animals that are mammals or birds, the optimal dosage varies
depending on whether it is used for therapeutic purposes or for
preventive purposes, and also varies with the type of infected
parasites, the type and extent of infection, dosage form, etc. But
generally, in case of oral administration, the dosage is in the
range from about 0.0001 to 10,000 mg per kilogram of body weight
per day. In case of parenteral administration, the dosage is in the
range from about 0.0001 to 10,000 mg per kilogram of body weight
per day, and the composition is administered in single or in
divided doses.
[1013] The concentration of the active ingredient in the
composition for exterminating animal parasites according to the
invention is typically from 0.0001 to 100% by weight, preferably
from 0.001 to 99% by weight, and more preferably from 0.005 to 80%
by weight. In general, the parasiticides may be provided as a
high-concentrated composition to be diluted to the appropriate
concentration prior to use.
[1014] In addition to the amide derivatives represented by Formula
(1) according to the invention, the composition for exterminating
animal parasites according to the invention can further contain
other insecticidal components that are generally known. The other
insecticidal components can include, for example, pyrethroid
compounds such as permethrin, d-phenothrin, allethrin, pyrethrum,
prallethrin, cyphenothrin, cyfluthrin, fenvalerate, fenpropathrin,
transfluthrin, metofluthrin, resmethrin, cypermethrin,
alpha-cypermethrin, bifenthrin, deltamethrin, lambda-cyhalothrin,
d,d-trans-cyphenothrin, tetramethrin, and ethofenprox; organic
phosphorus compounds such as dichlorvos, tetrachlorvinphos,
fenthion, chlorpyrifos, chlorpyrifos-methyl, malathion,
pirimiphos-methyl, fenitrothion, and diazinon; N-phenylpyrazole
compounds such as fipronil; carbamate compounds such as propoxur,
carbaryl, metoxadiazone, and fenocarb; neonicotinoid compounds such
as imidacloprid, clothianidin, thiamethoxam, acetamiprid,
nitenpyram, and dinotefuran; growth inhibitors for insect such as
methoprene, pyriproxyfen, lufenuron, fenoxycarb, triflumuron, and
chromafenozide; milbemycin oxime; milbemectin; lepimectin;
abamectin; ivermectin; selamectin; spinosad; rotenone; and the
like.
[1015] The disclosure of Japanese Patent Application JP 2010-019747
is incorporated herein in its entirety.
[1016] All publications, patent applications, and technical
specifications cited herein are incorporated herein by reference to
the same extent as if each individual publication, patent
application, and technical specification were specifically and
individually indicated to be incorporated by reference.
EXAMPLES
[1017] Representative Examples of the present invention will be
described with reference to the following Examples, but the present
invention is not limited thereto. In the present Examples, DMF
means N,N-dimethyl formamide, THF means tetrahydrofuran, IPE means
isopropyl ether, and DMI means 1,3-dimethyl-2-imidazolidinone.
[1018] Furthermore, "%" is based on mass unless specified
otherwise.
Example 1
Preparation of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(N-methylbenzamide)benzamide (Compound No. 7-1574).
##STR00243##
[1019] 1-1
Preparation of
4-(heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline
##STR00244##
[1021] 100 g (0.608 mol) of 2-(trifluoromethyl)aniline, 131 g
(0.639 mol) of 85% sodium hydrosulfite, and 20.9 g (0.0608 mol) of
tetrabutylammonium hydrogen sulfate were charged to a mixed
solution of 1500 ml of ethyl acetate and 1500 ml of water, and 53.9
g (0.639 mol) of sodium hydrogen carbonate was added thereto. 198 g
(0.669 mol) of heptafluoroisopropyl iodide was added dropwise
thereto at room temperature, followed by stirring at room
temperature for 6 hours. After the liquid separation, the solvent
of the organic layer was evaporated under reduced pressure, and 500
ml of ethyl acetate was charged thereto. 160 g (0.608 mol) of a 4 M
hydrogen chloride/ethyl acetate solution was added dropwise
thereto, followed by stirring at room temperature for 30 minutes,
and then stirring at 5.degree. C. for 1 hour. After the filtration,
the filtrate was washed with water and a saturated aqueous sodium
hydrogen carbonate in this order, and then dried over anhydrous
magnesium sulfate, and the solvent was evaporated under reduced
pressure. The obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=10:1) to
prepare 60.0 g (yield 30%) of a target compound.
[1022] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.49 (2H, broad-s),
6.81 (1H, d, J=8.3 Hz), 7.48 (1H, d, J=8.3 Hz), 7.64 (1H, s).
1-2
Preparation of
2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline
##STR00245##
[1024] 100 g (0.273 mol) of
4-(heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline was charged
to 500 ml of DMF, and 52.1 g (0.287 mol) of N-bromosuccinimide was
charged in separate portions thereto over 30 minutes. After
stirring at 60.degree. C. for 2 hours, and then cooling to room
temperature, the mixture was discharged to 2000 ml of water. The
mixture was extracted with ethyl acetate, then washed with
saturated brine, and dried over anhydrous magnesium sulfate. The
solvent was evaporated under reduced pressure and the obtained
residue was purified by silica gel column chromatography (eluent
solvent; hexane:ethyl acetate=20:1) to prepare 89.0 g (yield 80%)
of a target compound.
[1025] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.03 (2H, broad-s),
7.61 (1H, s), 7.79 (1H, s).
1-3
Preparation of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloro-
-3-nitrobenzamide
##STR00246##
[1027] 3.60 g (8.82 mmol) of
2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline was
charged to 20 ml of anhydrous THF, and cooled to -70.degree. C.
under a nitrogen atmosphere. 4.85 ml (9.70 mmol) of a 2.0 M lithium
diisopropyl amide hexane solution was added dropwise thereto, then
2.34 g (10.7 mmol) of acid chloride which was prepared from
2-chloro-3-nitrobenzoic acid and thionyl chloride was dissolved in
5 ml of anhydrous THF, and was added dropwise thereto, followed by
stirring at -70.degree. C. for 30 minutes and then stirring at room
temperature for 30 minutes. The mixture was discharged to an
aqueous ammonium chloride solution, then extracted with ethyl
acetate, and dried over anhydrous magnesium sulfate. The solvent
was evaporated under reduced pressure and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1.fwdarw.8:2.fwdarw.3:1) to prepare 1.76 g
(yield: 34%) of a target compound.
[1028] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.61 (1H, t, J=7.8
Hz), 7.67 (1H, broad-s), 7.93-7.97 (3H, m), 8.18 (1H, broad-s).
1-4
Preparation of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-nitrobenzamide
##STR00247##
[1030] To a solution of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-chloro-
-3-nitrobenzamide 4.89 g (8.27 mmol) in 50 ml of anhydrous DMF was
added 2.40 g (41.3 mmol) of potassium fluoride (spray-dried
product) under a flow of nitrogen, followed by stirring at
130.degree. C. for 10 hours. Liquid separation was carried out by
adding ethyl acetate, hexane, and water to the reaction mixture,
and then the organic layer was washed with water and saturated
brine, and dried over anhydrous magnesium sulfate. The solvent was
evaporated under reduced pressure and the obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1) to prepare 0.940 g (yield 20%) of a
target compound.
[1031] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.53 (1H, t, J=7.3
Hz), 7.93 (1H, broad-s), 8.17-8.18 (2H, m), 8.28-8.32 (1H, m),
8.44-8.48 (1H, m).
1-5
Preparation of
3-amino-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
2-fluorobenzamide
##STR00248##
[1033] 0.940 g (1.63 mmol) of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-nitrobenzamide and 0.960 g (5.05 mmol) of stannous chloride
(anhydrous) were added to 10 ml of ethanol, and 1.02 ml (9.78 mmol)
of concentrated hydrochloric acid was added thereto, followed by
stirring at 60.degree. C. for 4 hours. The reaction mixture was
adjusted to pH 10 by the addition of an aqueous sodium hydroxide
solution, and the precipitated insolubles were removed by
filtration using Celite. The filtrate on Celite was washed with
ethyl acetate. The filtrate was extracted with ethyl acetate, and
the organic layer was washed with a 20% aqueous sodium hydroxide
solution and saturated brine, and then dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=4:1) to
prepare 0.930 g (yield 99%) of a target compound.
[1034] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.49 (1H, m), 7.91
(1H, s), 8.14 (1H, s), 8.28 (1H, d, J=14.6 Hz).
1-6
Preparation of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(methylamino)benzamide
##STR00249##
[1036] 0.930 g (1.71 mmol) of
3-amino-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
2-fluorobenzamide was added to 5 ml of concentrated sulfuric acid,
and 10 ml of a 37% aqueous formaldehyde solution was charged
dropwise thereto at 40.degree. C. The reaction mixture was poured
into ice-water, adjusted to pH 10 using an aqueous sodium hydroxide
solution, and extracted with the addition of ethyl acetate. The
organic layer was washed with a 20% aqueous sodium hydroxide
solution and saturated brine, and then dried over anhydrous
magnesium sulfate. The solvent was evaporated under reduced
pressure and the obtained residue was purified by silica gel column
chromatography (eluent solvent; hexane:ethyl acetate=8:1) to
prepare 0.690 g (yield 72%) of a target compound.
[1037] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.94 (3H, s), 4.14
(1H, broad-s), 6.88-6.93 (1H, m), 7.18 (1H, t, J=7.8 Hz), 7.37-7.41
(1H, m), 7.90 (1H, s), 8.13 (1H, s), 8.27 (1H, d, J=14.6 Hz).
<1-7> Preparation of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(N-methylbenzamide)benzamide (Compound No. 7-1574)
##STR00250##
[1039] To a solution of 1.54 g (2.75 mmol) of
N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-
-3-(methylamino)benzamide and 0.330 g (4.13 mmol) of pyridine in 5
ml of THF was added 0.460 g (3.30 mmol) of benzoyl chloride,
followed by stirring at 60.degree. C. for 5 hours. To the reaction
mixture were added water and ethyl acetate, and the organic layer
was washed with 1 M hydrochloric acid, a saturated aqueous sodium
hydrogen carbonate solution, and saturated brine, and then dried
over anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure and the obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=8:1), and the obtained solid was washed with IPE to prepare
1.45 g (yield 80%) of a target compound.
[1040] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.50 (3H, s),
6.99-7.33 (6H, m), 7.43-7.45 (1H, m), 7.90 (1H, s), 7.97-8.06 (2H,
m), 8.13 (1H, s).
Example 2
Preparation of
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenz-
amide)benzamide (Compound No. 7-1104)
##STR00251##
[1041] 2-1
Preparation of 4-(heptafluoropropan-2-yl)aniline
##STR00252##
[1043] 100 g (1.02 mol) of aniline, 230 g (1.12 mol) of 85% sodium
hydrosulfite, and 35.1 g (0.100 mol) of tetrabutylammonium hydrogen
sulfate were charged to a mixed solution of 1500 ml of t-butyl
methyl ether and 1500 ml of water, and 94.7 g (1.12 mol) of sodium
hydrogen carbonate was added thereto. 350 g (1.12 mol) of
heptafluoroisopropyl iodide was added dropwise thereto at room
temperature, followed by stirring at room temperature for 6 hours.
After the liquid separation, the organic layer was washed with 1 M
hydrochloric acid, water, and a saturated aqueous sodium hydrogen
carbonate solution, and then dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure, and 500 ml of
ethyl acetate was charged thereto. 255 g (1.02 mol) of a 4 M
hydrogen chloride/ethyl acetate solution was added dropwise
thereto, followed by stirring at room temperature for 30 minutes
and at 5.degree. C. for 1 hour. The precipitated solid was
separated by filtration, and the solid was charged to 1000 ml of
ethyl acetate, adjusted to pH 8 to 9 by the addition of 1000 ml of
a saturated aqueous sodium hydrogen carbonate solution at
20.degree. C. or lower, and subjected to liquid separation. The
organic layer was dried over anhydrous sodium sulfate, and then the
solvent was evaporated under reduced pressure to prepare 188 g
(yield 71%) of a target compound.
[1044] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
6.69-6.74 (2H, m), 7.35 (2H, d, J=9.3 Hz).
2-2
Preparation of 2,6-dibromo-4-(heptafluoropropan-2-yl)aniline
##STR00253##
[1046] 216 g (0.802 mol) of 4-(heptafluoropropan-2-yl)aniline was
charged to 863 ml of DMF, followed by cooling to 5.degree. C. 285 g
(1.60 mol) of N-bromosuccinimide was charged in separate portions
thereto over 1 hour. The mixture was stirred at room temperature
for 1 hour and then stirred at 37.degree. C. for 2 hours. The
mixture was discharged to 2000 ml of water, extracted with 2000 ml
of ethyl acetate, and washed with 1000 ml of saturated brine. After
dried over anhydrous magnesium sulfate, the solvent was evaporated
under reduced pressure. The obtained residue was purified by silica
gel column chromatography (eluent solvent; hexane:ethyl
acetate=20:1) to prepare 304 g (yield 90%) of a target
compound.
[1047] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.88 (2H, broad-s),
7.59 (2H, s).
2-3
Preparation of
2-chloro-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-3-nitrobenzamid-
e
##STR00254##
[1049] According to the method of 1-3 of Example 1, a target
compound was prepared from
2,6-dibromo-4-(heptafluoropropan-2-yl)aniline
[1050] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.58 (1H, t, J=7.8
Hz), 7.66 (1H, broad-s), 7.90 (2H, s), 7.93 (1H, dd, J=1.5, 7.8
Hz), 7.98 (1H, d, J=7.8 Hz).
2-4
Preparation of
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamid-
e
##STR00255##
[1052] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-3-nitrobenzamid-
e.
[1053] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.51-7.55 (1H, m),
7.90 (2H, s), 8.16 (1H, d, J=11.7 Hz), 8.27-8.31 (1H, m), 8.48 (1H,
t, J=6.3 Hz).
2-5
Preparation of
3-amino-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenzamid-
e
##STR00256##
[1055] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamid-
e.
[1056] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.49 (1H, m), 7.91
(1H, s), 8.14 (1H, s), 8.28 (1H, d, J=14.6 Hz).
2-6
Preparation of
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(methylamino)-
benzamide
##STR00257##
[1058] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenzamid-
e.
[1059] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.94 (3H, d, J=5.6
HZ), 4.87-4.91 (1H, m), 6.91 (1H, t, J=7.9 Hz), 7.18 (1H, t, J=7.9
Hz), 7.41 (1H, t, J=7.1 Hz), 7.87 (2H, s), 8.20 (1H, d, J=13.5
Hz).
2-7
Preparation of
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(N-methylbenz-
amide)benzamide (Compound No. 7-1104)
##STR00258##
[1061] According to the method of 1-7 of Example 1, a target
compound was prepared from
N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-(methylamino)-
benzamide and benzoyl chloride.
[1062] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.51 (3H, s),
7.22-7.44 (7H, m), 7.86 (2H, s), 8.00-8.03 (2H, m).
Example 3
Preparation of
3-benzamide-2-fluoro-N-(4-(heptafluoropropan-2-yl)-2,6-bis(trifluoromethy-
l)phenyl)benzamide (Compound No. 6-2110)
##STR00259##
[1063] 3-1
Preparation of 2,6-diiodo-4-(heptafluoropropan-2-yl)aniline
##STR00260##
[1065] To a solution of 5.74 g (22.0 mmol) of
4-(heptafluoropropan-2-yl)aniline obtained in 2-1 of Example 2 in
50 ml of ethanol was added 2.16 g (22.0 mmol) of concentrated
sulfuric acid at 5.degree. C. The reaction mixture was warmed to
room temperature, and 10.0 g (44.0 mmol) of N-iodosuccinimide was
added thereto, followed by stirring for 3 hours. The reaction
mixture was neutralized with a saturated aqueous sodium hydrogen
carbonate solution. The precipitated crystals were filtered, washed
with water, and then dried to prepare 9.00 g (yield 80%) of a
target compound.
[1066] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.95 (2H, broad-s),
7.79 (2H, s).
3-2
Preparation of
2-chloro-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-3-nitrobenzamide
##STR00261##
[1068] To a solution of 40.0 g (78.0 mmol) of
2,6-diiodo-4-(heptafluoropropan-2-yl)aniline in 100 ml of DMI was
added 20.6 g (94.0 mmol) of 2-chloro-3-nitrobenzoyl chloride,
followed by stirring at 135.degree. C. for 3 hours. After cooling
to room temperature, the reaction mixture was poured into 1000 ml
of water. After extraction with the addition of 1000 ml of ethyl
acetate, the organic layer was washed with water and then dried
over anhydrous magnesium sulfate. The solvent was evaporated under
reduced pressure and the obtained residue was washed with hexane to
prepare 56.2 g (yield 99%) of a target compound.
[1069] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.58 (1H, t, J=8.3
Hz), 7.70 (1H, d, J=3.4 Hz), 7.93 (1H, dd, J=1.5, 6.3 Hz),
8.08-8.10 (1H, m), 8.13 (2H, s).
3-3
Preparation of
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide
##STR00262##
[1071] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-3-nitrobenzamide
[1072] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.52-7.55 (1H, m),
8.12-8.18 (3H, m), 8.29-8.32 (1H, m), 8.48-8.51 (1H, m).
3-4
Preparation of
3-amino-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenzamide
##STR00263##
[1074] According to the method of 1-5 of Example 1, a target
compound was prepared from
N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluoro-3-nitrobenzamide-
.
[1075] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.93 (2H, broad-s),
6.99-7.04 (1H, m), 7.08 (1H, t, J=7.8 Hz), 7.39-7.43 (1H, m), 8.10
(2H, s), 8.72 (1H, d, J=11.2 Hz).
3-5
Preparation of
3-benzamide-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenza-
mide (Compound No. 6-1260)
##STR00264##
[1077] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenzamide-
.
[1078] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.39 (1H, t, J=7.8
Hz), 7.52-7.57 (4H, m), 7.60-7.63 (2H, m), 7.93-7.94 (4H, m), 8.70
(1H, t, J=6.3 Hz).
3-6
Preparation of
3-benzamide-2-fluoro-N-(4-(heptafluoropropan-2-yl)-2,6-bis(trifluoromethy-
l)phenyl)benzamide (Compound No. 6-2110)
##STR00265##
[1080] A solution of 1.95 g (2.59 mmol) of
3-benzamide-N-(2,6-diiodo-4-(heptafluoropropan-2-yl)phenyl)-2-fluorobenza-
mide, 0.10 g (0.520 mmol) of copper iodide, and 1.24 g (6.48 mmol)
of methyl fluorosulfonyl difluoroacetate in 50 ml of DMF was
stirred at 100.degree. C. for 6 hours. The reaction mixture was
cooled to room temperature, and then 10 ml of water and 100 ml of
ethyl acetate were added thereto, followed by filtration through
Celite. The organic layer of the liquid was washed with water and a
saturated aqueous sodium hydrogen carbonate solution, and then
dried over anhydrous magnesium sulfate. The solvent was evaporated
under reduced pressure and the obtained residue was purified by
silica gel column chromatography (eluent solvent; hexane:ethyl
acetate=1:1). The obtained solid was washed with hexane to prepare
0.840 g (yield 51%) of a target compound.
[1081] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.36-7.40 (1H, m),
7.53-7.64 (3H, m), 7.84-7.97 (1H, m), 7.92-7.94 (2H, m), 8.04-8.07
(1H, m), 8.08-8.13 (1H, m), 8.20 (2H, s), 8.68-8.72 (1H, m).
Example 4
Preparation of
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide (Compound No. 7-1733)
##STR00266##
[1082] 4-1
Preparation of
2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline
##STR00267##
[1084] To 1200 mL of ethanol was added 200 g (0.600 mol) of
4-(heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline which was
obtained in 1-1 of example 1, and 63.2 g (0.630 mol) of
concentrated sulfuric acid and 155 g (0.660 mol) of
N-iodosuccinimide were added thereto under ice-cooling, followed by
stirring at room temperature for 1 hour and 30 minutes and at
40.degree. C. for 4 hours. To the reaction solution was added a 4 M
aqueous sodium hydroxide solution to neutralize the reaction
solution, and then ethyl acetate was added thereto to extract the
organic phase. The organic phase was washed with saturated brine,
and dried over anhydrous magnesium sulfate, and then the solvent
was evaporated under reduced pressure. The obtained residue was
purified by silica gel column chromatography (eluent solvent;
hexane:ethyl acetate=10:1) to prepare 216 g (yield 80%) of a target
compound.
[1085] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 5.04 (2H, broad-s),
7.64 (1H, s), 7.99 (1H, s).
4-2
Preparation of
2-chloro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-nitrobenzamide
##STR00268##
[1087] According to the method of 3-2 of Example 3, a target
compound was prepared from
2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline and
2-chloro-3-nitrobenzoyl chloride.
[1088] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.60 (1H, t, J=7.8
Hz), 7.76 (1H, s), 7.94 (1H, dd, J=1.5, 7.8 Hz), 7.97 (1H, s), 8.03
(1H, dd, J=1.5, 7.8 Hz), 8.39 (1H, s).
4-3
Preparation of
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-nitrobenzamide
##STR00269##
[1090] According to the method of 1-4 of Example 1, a target
compound was prepared from
2-chloro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-nitrobenzamide.
[1091] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.51-7.55 (1H, m),
7.97 (1H, s), 8.23 (1H, d, J=12.2 Hz), 8.28-8.32 (1H, m), 8.37 (1H,
s), 8.44-8.48 (1H, m).
4-4
Preparation of
3-amino-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)-
phenyl)benzamide
##STR00270##
[1093] According to the method of 1-5 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-nitrobenzamide.
[1094] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.92 (2H, broad-s),
7.02-7.04 (1H, m), 7.11 (1H, t, J=7.8 Hz), 7.47-7.52 (1H, m), 7.94
(1H, s), 8.30-8.35 (2H, m).
4-5
Preparation of
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-(methylamino)benzamide
##STR00271##
[1096] According to the method of 1-6 of Example 1, a target
compound was prepared from
3-amino-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)-
phenyl)benzamide
[1097] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.95 (3H, s), 4.15
(1H, broad-s), 6.90 (1H, t, J=8.2 Hz), 7.19 (1H, t, J=7.8 Hz), 7.40
(1H, t, J=7.8 Hz), 7.92 (1H, s), 8.30 (1H, s), 8.34 (1H, s).
4-6
Preparation of
2-fluoro-3-(4-fluoro-N-methylbenzamide)-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide (Compound No. 7-1733)
##STR00272##
[1099] According to the method of 1-7 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-(methylamino)benzamide and 4-fluorobenzoyl chloride.
[1100] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.50 (3H, s), 6.91
(2H, s), 6.93-7.35 (3H, m), 7.46 (1H, t, J=7.0 Hz), 7.93 (1H, s),
8.01-8.10 (1H, m), 8.13 (1H, broad-s), 8.34 (1H, s).
Example 5
Preparation of
2-fluoro-3-(3-fluoro-N-methylbenzamide)-N-(2-iodo-4-(heptafluoropropan-2--
yl)-6-(trifluoromethyl)phenyl)benzamide (Compound No. 7-1732)
##STR00273##
[1102] According to the method of 1-7 of Example 1, a target
compound was prepared from
2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)--
3-(methylamino)benzamide and 3-fluorobenzoyl chloride.
[1103] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.50 (3H, s), 6.91
(2H, s), 7.00-7.18 (4H, m), 7.27-7.31 (1H, m), 7.45-7.48 (1H, m),
7.93 (1H, s), 8.01-8.03 (1H, m), 8.12 (1H, broad-s), 8.34 (1H,
s).
Example 6
Preparation of
2-fluoro-3-(4-fluorobenzamide)-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(tr-
ifluoromethyl)phenyl)benzamide (Compound No. 6-1733)
##STR00274##
[1105] According to the method of 1-7 of Example 1, a target
compound was prepared from
3-amino-2-fluoro-N-(2-iodo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)-
phenyl)benzamide and 4-fluorobenzoyl chloride.
[1106] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.19-7.25 (2H, m),
7.35 (1H, t, J=7.8 Hz), 7.87-7.97 (4H, m), 8.08 (1H, s), 8.25 (1H,
d, J=12.0 Hz), 8.37 (1H, s), 8.65 (1H, t, J=8.0 Hz).
[1107] Now, the representative examples of the formulations
according to the invention will be shown, although the invention is
not limited thereto. "Parts" in Formulation Examples indicates
"parts by weight".
Formulation Example 1
Emulsion
[1108] 10 parts of Compound No. 7-1574 or 7-1733, 6 parts of Sol
Pol 355S (surfactant available from Toho Chemical Industry Co.),
and 84 parts of Solvesso 150 (available from ExxonMobil Chemical
Co.) were homogeneously mixed with stirring to obtain as emulsion
the composition for exterminating animal parasites.
Formulation Example 2
Ointment
[1109] 1 part of Compound No. 7-1574 or 7-1733, 50 parts of white
beeswax, and 49 parts of white petrolatum were thoroughly mixed to
obtain as ointment the composition for exterminating animal
parasites.
Formulation Example 3
Tablets
[1110] 2 parts of Compound No. 7-1574 or 7-1733, 10 parts of
vegetable oil (olive oil), 3 parts of crystalline cellulose, 20
parts of white carbon, and 65 parts of kaolin were thoroughly mixed
and then compressed to obtain as tablets the composition for
exterminating animal parasites.
Formulation Example 4
Injectable
[1111] 10 parts of Compound No. 7-1574 or 7-1733, 10 parts of
propylene glycol for food additives, 80 parts of vegetable oil
(corn oil) were mixed to obtain as injectable the composition for
exterminating animal parasites.
Formulation Example 5
Solution
[1112] 5 parts of Compound No. 7-1574 or 7-1733, 20 parts of
surfactant, and 75 parts of ion-exchanged water were thoroughly
mixed to obtain as solution the composition for exterminating
animal parasites.
[1113] Next, the utility of the composition of the invention as a
parasiticide will be concretely explained in the following Test
Examples, although the invention is not limited thereto.
Test Example 1
[1114] Insecticidal Test for Ctenocephalides Felis
[1115] 0.5 ml of a solution of acetone, the active ingredient,
prepared to the prescribed concentration was added dropwise to a
glass tube with a flat bottom (internal diameter: 2.6 cm, bottom
area: 5.3 cm.sup.2, height: 12 cm), and the solvent was evaporated
at room temperature to form a dry film of the agent on the bottom
surface. About 10 adults of Ctenocephalides Felis per glass tube
were added, and the adults were contact-exposed to the test
compound. After 24 hours of the exposure, the conditions of the
adults were examined and classified into "alive" and "dead
(including a moribund condition)" to determine the death rate (in
triplicate). The results are shown in Table A4.
[1116] As the comparative compounds, the following Compounds (A),
(B), and (C) disclosed in WO2009/080203, and fipronil were
used.
TABLE-US-00056 TABLE A4 active ingredient concentration death rate
(compound number) (.mu.g/ml) (%) 7-1574 0.1 100.0 7-1733 0.1 100.0
7-1732 0.1 76.7 6-1733 0.1 70.0 7-1104 0.1 73.3 compound (A) 1.0
0.0 compound (B) 1.0 3.2 compound (C) 1.0 0.0 fipronil 0.1 92.1
only acetone -- 4.7 ##STR00275## ##STR00276## ##STR00277##
[1117] The amide derivatives of Compound No. 7-1574 and 7-1104 were
found to be effective even in the examination after 12 hours of the
exposure. In addition, they showed immediate effect as compared
with the fipronil.
Test Example 2
[1118] Insecticidal Test for Haemaphyxalis longicornis
[1119] 1 ml of a solution of acetone, the active ingredient,
prepared to the prescribed concentration was added dropwise to
filter paper inside a petri dish with a diameter of 9 cm, and the
acetone was evaporated at room temperature. About 100 larvae of
Haemaphyxalis longicornis per dish were added to the filter paper.
The dish was covered by a polyethylene sheet, sealed with a rubber
band, and placed in a dark place at a temperature of 25.degree. C.
and a relative humidity of 100% to expose the larvae to the test
substance. After 24 hours of the exposure, the conditions of the
larvae were examined and classified into "alive" and "dead
(including a moribund condition)".
[1120] As a result, the amide derivatives according to the
invention were found to be effective in killing Haemaphyxalis
longicornis.
Test Example 3
[1121] Insecticidal Test for Ctenocephalides felis
[1122] 0.96 ml of a solution of acetone, the active ingredient,
prepared to the prescribed concentration was added dropwise to a
glass tube with a flat bottom (internal diameter: 3.6 cm, height:
12 cm), and the solvent was evaporated at room temperature to form
a dry film of the agent on the bottom surface. About 10 adults of
Ctenocephalides felis per glass tube were added, and they were
contact-exposed to the test compound. After 24 hours of the
exposure, the conditions of the adults were examined and classified
into "alive" and "dead (including a moribund condition)" to
determine the death rate was determined (in triplicate). The
results are shown in Table A5.
[1123] As the comparative compounds, the following Compounds (D)
and (E) disclosed in WO2009/080203, and fipronil were used.
TABLE-US-00057 TABLE A5 active ingredient concentration death rate
(compound number) (.mu.g/ml) (%) 7-1574 0.03 72.0 0.1 98.9 7-1733
0.03 21.1 0.1 91.6 compound (D) 0.3 22.0 1 61.4 compound (E) 1 0.0
fipronil 0.03 70.0 0.1 100.0 only acetone -- 1.4 ##STR00278##
##STR00279##
Test Example 4
[1124] Insecticidal Test for Rhipicephalus sanguineus
[1125] 0.5 ml of a solution of acetone, the active ingredient,
prepared to the prescribed dose was added dropwise into a glass
petri dish with a diameter of 10 cm, and the acetone was evaporated
at room temperature. About 10 adults of Rhipicephalus sanguineus
per dish were added, and the dish was covered by another glass
petri dish that was treated with the active ingredient in the same
manner described above. After 18 hour exposure to the test
substance, the adults were transferred into a glass petri dish that
was not treated with the active ingredient. After 48 hours of the
exposure, the conditions of the adults were examined and classified
into "alive" and "dead (including a moribund condition)" to
determine the death rate (in single). The results are shown in
Table A6.
[1126] As the comparative compounds, said Compounds (B), (C), and
(D), and the following Compound (F) disclosed in WO2009/080203, and
fipronil were used.
TABLE-US-00058 TABLE A6 active ingredient concentration death rate
(compound number) (mg/m.sup.2) (%) 7-1574 0.0431 10.0 0.0861 100.0
0.172 100.0 7-1733 0.0431 0.0 0.0861 80.0 0.172 100.0 compound (B)
0.673 0.0 2.69 20.0 10.8 50.0 compound (C) 0.673 0.0 2.69 11.1 10.8
10.0 compound (D) 0.673 0.0 2.69 10.0 10.8 50.0 compound (F) 0.673
0.0 2.69 0.0 10.8 0.0 fipronil 0.0431 0.0 0.172 45.5 0.673 100.0
##STR00280##
[1127] As the composition for exterminating animal parasites
according to the invention has excellent activity for exterminating
animal parasites, the composition has wide industrial
applicability.
[1128] The foregoing description of the exemplary embodiments of
the present invention has been provided for the purposes of
illustration and description. It is not intended to be exhaustive
or to limit the invention to the precise forms disclosed.
Obviously, many modifications and variations will be apparent to
practitioners skilled in the art. The exemplary embodiments were
chosen and described in order to best explain the principles of the
invention and its practical applications, thereby enabling others
skilled in the art to understand the invention for various
embodiments and with the various modifications as are suited to the
particular use contemplated. It is intended that the scope of the
invention be defined by the following claims and their
equivalents.
[1129] All publications, patent applications, and technical
standards mentioned in this specification are herein incorporated
by reference to the same extent as if each individual publication,
patent application, or technical standard was specifically and
individually indicated to be incorporated by reference.
TABLE-US-LTS-00001 LENGTHY TABLES The patent application contains a
lengthy table section. A copy of the table is available in
electronic form from the USPTO web site
(http://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20110201687A1).
An electronic copy of the table will also be available from the
USPTO upon request and payment of the fee set forth in 37 CFR
1.19(b)(3).
* * * * *
References